International Journal of Pharma and Bio Sciences
|
|
- Gavin Sharp
- 6 years ago
- Views:
Transcription
1 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL IDU SIGH, HEMLATA KAU, SUIL KUMA, AU KUMA** AD ASHK KUMA* * Medicinal Chemistry Division, Department of Pharmacology, L.L..M. Medical College, Meerut , U. P. India ** Department of SPM, L.L..M. Medical College, Meerut , U. P. India. *Corresponding author ashokraj.kumar744@gmail.com ABSTACT A series of -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-(3-chloro-2-(substitutedphenyl)-4- oxoazetidin-1-yl)-5-(pyridin-4-yl)-5-thio)acetamido-1,2,4-triazoles (5a-5g) have been prepared by the condensation of 6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl-2-(4-(substitutedbenzylideneamino)-5-(pyridin-4- yl)-3-thio)acetamido-1,2,4-triazoles (4a-4g) with chloroacetyl chloride in presence of trimethylamine. -(6- bromo-2-methyl-4-oxoquinazolin-3(4h)-yl)-2-(4-(2-(substitutedphenyl)-4-oxothiazolidin-3-yl)-5-(pyridin-4-yl)- 3-thio)acetamido-1,2,4-triazoles (6a-6g) have been synthesized by the reaction of compounds 4a-4g with thioglycolic acid in presence of anhydrous zinc chloride. All the newly synthesized compounds were screened for their antibacterial activity against S.aureus, E.coli, P.vulgaris, K. pneumoniae. Structures of all the compounds were established by elemental and spectral (I, 1 H M and Mass) analysis. KEYWD Pyridinyltriazoles, Quinazolinyltriazoles, Azetidinonyltriazoles, Thiazolidinonyltriazoles. ITDUCTI It has been reported that triazole is the biodynamic heterocyclic moiety. Several triazole derivatives have also been reported to show significant antibacterial 1, antifungal 2, anticonvulsant 3 and anti-inflammatory 4 activities. Screening the literature reveals that pyridine 5 and quinazolinone 6 1 derivatives also exhibited antibacterial activity. The scientific literature reveals that this activity is due to presence of azetidinones 7 and thiazolidinones 8 moieties in a molecule and change in activity depends on the nature of substituents. In light of above observations it was thought worthwhile to synthesized some new substituted triazole derivatives by
2 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL incorporation of pyridine, quinazolinone, azetidinone compounds were administered by i.p. route in one and thiazolidinone moieties with the hope to get group and the same volume of propylene glycol in better antibacterial agents. MATEIAL AD METHDS All the synthesized compounds were tested for their antibacterial activity. The effect of unknown compounds were compared with the standard drugs ampicillin and gattifloxacin. The propylene glycol treated group served as control. All the newly synthesized compounds were also screened for their approximate lethal dose (ALD 50 ). Cup-Plate Method (CUPS): This activity was performed by following the method of Chuinckshank et. al. 9 in albino rats. utrient agar was poured onto the sterilized petri dishes (20-25 ml each pertri dish). The poured material was allowed to set (1-1.5 h) and thereafter the CUPS (10 mm diameter) were made by punching into the agar surface with a sterile cork borer and scooping out the punched part of the agar. Into these cups the test compound solution was added with the help of sterile syringe. The plates were incubated at 37 0 C for 48 h and the results were noted. A solvent control (10% DMS in methanol) was also run to not the activity of the blank (solvent). The above said standard drugs were also screened under similar conditions for comparison. Approximate lethal dose (ALD 50 ): The LD 50 was determined in albino rats weighing gm of either sex by the method of Smith 10. The test another group of animals consisting six rats in graded doses. The animals were allowed to take food and water adlibidum. After 24 h of drug administration percent mortality in each group was observed. From the data obtained ALD 50 was calculated. EXPEIMETAL 4-amino-5-pyridine-3-mercapto-1, 2, 4-triazole (1) A solution of pyridine potassium dithiocarbazinate (1.5 mol) in water (5 ml) and hydrazine hydrate ( 1.5 mol) was refluxed for 10 h. The colour of the reaction mixture changed to green with the evolution of hydrogen sulfide gas. The reaction mixture was cooled at room temperature and diluted with water (100 ml). n acidification with concentrated HCl the required triazole (1) was precipitated, which was filtered, washed thoroughly with cooled water and recrystallized from acetone to furnish compound 1. Yield 95%; m.p C. I (KBr, ν max in cm -1 ): 3380 (H 2 ), 3132 (aromatic CH), 2585 (SH), 1612 (C=C of aromatic ring), 1608 (C=), 1281 (-). 1 HM (CDCl 3 + DMS-d 6 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), (m, 4H, Ar-H), 5.72 (s, 2H, H 2 exchangeable with D 2 ). MS: [M] + at m/z Anal. Calcd. for C 7 H 7 5 S: C, 43.51; H, 3.65;, 36.24: Found: C, 43.45; H, 3.94;, 36.49%. 2
3 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL C H 2 H 2. H 2 CHH 2 CS 2 /KH H 2 H 2. H 2 CH 3 CH (1) H 2 SH CH SH (2a-g) CH ClCH 2 CCl SCH 2 CCl CH (3a-g) H 2 Br = 4-H & 3-CH 3, 2,4-Cl, 2,6-Cl, 2,4-Br, 2,6-Br, 2-H, 4-(CH 3 ) 2 SCH 2 CH CH (4a-g) Br ClCH 2 CCl/Et 3 HSCH/Anhy.ZnCl 2 SCH 2 CH H C Cl (5a-g) Br SCH 2 CH H C S (6a-g) Br SCHEME-1 3
4 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL General procedure for synthesis of 4- (substitutedbenzylideneamino)-5-(pyridin-4-yl)-4h- 3-mercapto-1,2,4-triazoles (2a-2g) A solution of compound (1) (0.5 mol) and various substituted aromatic aldehydes (0.5 mol) in 40 ml of ethanol along with glacial acetic acid (2-3 drops) were refluxed for 2 h. The completion of the reaction checked by TLC. The reaction mixtures were cooled, filtered and washed with ethanol, dried and recrystallization with DMF, water to yield compound 2a-2g. 4-(4-hydroxy-3-methoxybenzylideneamino)-5- (pyridin-4-yl)-4h-3-mercapto-1,2,4-triazole (2a) Yield 93% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 3451 (H), 3133 (aromatic CH), 2581 (SH), 1645 (C=), 1612 (C=C of aromatic ring), 1592 (=CH), 1492 (-), 1453 (C-), 1224 (CH 3 ). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, H exchangeable with D 2 ), (s, 1H, SH exchangeable with D 2 ), 8.86 (s, 1H, =CH), (m, 7H, Ar-H), 3.36 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 15 H S: C, 55.03; H, 4.00.;, 21.39: Found: C, 55.21; H, 4.25;, 21.30% 4-(2,4-dichlorobenzylideneamino)-5-(pyridin-4-yl)- 4H-3-mercapto-1,2,4-triazole (2b) Yield 91% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 2581 (SH), 1647 (C=), 1614 (C=C of aromatic ring), 1592 (=CH), 1493 (-), 1454 (C-), 760 (C-Cl). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), 8.87 (s, 1H, =CH), (m, 7H, Ar-H). MS: [M] + at m/z Anal. Calcd. for C 14 H 9 Cl 2 5 S: C, 48.01; H, 2.59;, 20.00: Found: C, 48.32; H, 2.79;, 2.25% 4-(2,6-dichlorobenzylideneamino)-5-(pyridine-4-yl)- 4H-3-mercapto-1,2,4-triazole (2c) Yield 90% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 2581 (SH), 1647 (C=), 1614 (C=C of aromatic ring), 1591 (=CH), 1493 (-), 1455 (C-), 760 (C-Cl). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), 8.86 (s, 1H, =CH), (m, 7H, Ar-H). MS: [M] + at m/z Anal. Calcd. for C 14 H 9 Cl 2 5 S: C, 48.01; H, 2.59;, 20.00: Found: C, 48.23; H, 2.77;, 20.26% 4-(2,4-dibromobenzylideneamino)-5-(pyridin-4-yl)- 4H-3-mercapto-1,2,4-triazole (2d) Yield 87% (Petrolium ether); m.p C. I (KBr, ν max in cm -1 ): 3133 (aromatic CH), 2583 (SH), 1648 (C=), 1616 (C=C of aromatic ring), 1591 (=CH), 1494 (-), 1454 (C-), 610 (C-Br). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), 8.88 (s, 1H, =CH), (m, 7H, Ar-H). MS: [M] + at m/z Anal. Calcd. for C 14 H 9 Br 2 5 S: C, 38.29; H, 2.07;, 15.95: Found: C, 38.55; H, 2.26;, 15.76% 4-(2,6-dibromobenzylideneamino)-5-(pyridin-4-yl)- 4H-3-mercapto-1,2,4-triazole (2e) Yield 86% (Ethanol); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 2584 (SH), 1647 (C=), 1614 (C=C of aromatic ring), 1592 (=CH), 1493 (-), 1457(C-), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), 8.86 (s, 1H, =CH), (m, 7H, Ar-H). MS: [M] + at m/z Anal. Calcd. for C 14 H 9 Br 2 5 S: C, 38.29; H, 2.07;, 15.95: Found: C, 38.55; H, 2.26;, 15.76% 4-(4-hydroxybenzylideneamino)-5-(pyridin-4-yl)- 4H-3-mercapto-1,2,4-triazole (2f) Yield 84% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 3450(H), 3134 (aromatic CH), 2581 (SH), 4
5 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL 1647 (C=), 1614 (C=C of aromatic ring), 1591 (=CH), 1495 (-), 1455 (C-). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, H exchangeable with D 2 ), (s, 1H, SH exchangeable with D 2 ), 8.87 (s,1h, =CH), (m, 8H, Ar-H). MS: [M] + at m/z Anal. Calcd. for C 14 H 11 5 S: C, 56.55; H, 3.73;, 23.55: Found: C, 56.84; H, 3.54;, 23.76% 4-(4-(dimethylamino)benzylideneamino)-5-(pyridin- 4-yl)-4H-3-mercapto-1,2,4-triazole (2g) Yield 83% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 2585 (SH), 1648 (C=), 1614(C=C of aromatic ring), 1592 (=CH), 1493 (-), 1453 (C-). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, SH exchangeable with D 2 ), 8.87 (s, 1H, =CH), (m, 8H, Ar-H), 2.32 (s, 6H, (CH 3 ) 2 ). MS: [M] + at m/z Anal. Calcd. for C 16 H 16 6 S: C, 59.24; H, 4.97;, 25.91: Found: C, 59.46; H, 4.75;, 25.75% General procedure for synthesis of 4- (substitutedbenzylideneamino)-5-(pyridin-4-yl)-3- thioacetylchlorid-1,2,4-triazoles (3a-3g) A mixture of compounds 2a-2g (0.1 mol) in dry diethylether (10 ml) and triethylamine (0.03 mol), choroacetyl chloride (0.15 mol) was added dropwise with stirring between C. After completion of addition the stirring was continued at room temperature. The reaction mixtures were then kept for 46 to 50 h at room temperature. Finally, the reaction mixtures were added to ice cold water to obtain the final product. It was dried and purified by recrystallization from appropriate solvents to obtained compounds 3a-3g. Yield 81% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 3451(H), 3132 (aromatic CH), 1647 (C=), 1614 (C=C of aromatic ring), 1592 (=CH), 1493 (-), 1455 (C-), 1226 (CH 3 ), 682 (C-S-C). 1 HM (CDCl 3 ) δ in ppm: (s, 1H, H exchangeable with D 2 ), 8.85 (s, 1H, =CH), (m, 7H, Ar-H), 4.45 (s, 2H, S-CH 2 -C), 3.38 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 17 H 14 Cl 5 3 S: C, 50.56; H, 3.49;, 17.34: Found: C, 50.87; H, 3.68;, 17.55% 4-(2,4-dichlorobenzylideneamino)-5-(pyridin-4-yl)- 3-thioacetylchlorid-1,2,4-triazole (3b) Yield 80% (Petroleum ether); m.p C. I (KBr, ν max in cm -1 ): 3135 (aromatic CH), 1649 (C=), 1615 (C=C of aromatic ring), 1595 (=CH), 1490 (-), 1454 (C-), 682 (C-S-C), 762 (C-Cl). 1 HM (CDCl 3 ) δ in ppm: 8.86 (s, 1H, =CH), (m, 7H, Ar-H), 4.47 (s, 2H, S-CH 2 -C). MS: [M] + at m/z Anal. Calcd. for C 16 H 10 Cl 3 5 S: C, 45.04; H, 2.36;, 16.41: Found: C, 45.25; H, 2.65;, 16.76% 4-(2,6-dichlorobenzylideneamino)-5-(pyridin-4-yl)- 3-thioacetylchlorid-1,2,4-triazole (3c) Yield 79% (Ethanol); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 1647 (C=), 1614 (C=C of aromatic ring), 1592 (=CH), 1493 (-), 1455 (C-), 681 (C-S-C), 760 (C-Cl). 1 HM (CDCl 3 ) δ in ppm: 8.88 (s, 1H, =CH), (m, 7H, Ar- H), 4.45 (s, 2H, S-CH 2 -C). MS: [M] + at m/z Anal. Calcd. for C 16 H 10 Cl 3 5 S: C, 45.04; H, 2.36;, 16.41: Found: C, 45.25; H, 2.65;, 16.76% 4-(2,4-dibromobenzylideneamino)-5-(pyridin-4-yl)- 3-thioacetylchlorid-1,2,4-triazole (3d) Yield 77% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 3135 (aromatic CH), 1646 (C=), 1617 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1458 (C-), 682(C-S-C), 612 (C-Br). 1 HM (CDCl 3 ) δ in ppm: 8.86 (s, 1H, =CH), (m, 7H, Ar-H), 4.47 (s, 2H, S-CH 2 -C). MS: [M] + at m/z Anal. Calcd. for 5
6 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL C 16 H 10 Br 2 Cl 5 S: C, 37.27; H, 1.95;, 13.58: Found: C, 37.56; H, 1.76;, 13.69% 4-(2,6-dibromobenzylideneamino)-5-(pyridin-4-yl)- 3-thioacetylchlorid-1,2,4-triazole (3e) Yield 76% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 1645 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1495 (-), 1455 (C-), 681 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm: 8.87 (s, 1H, =CH), (m, 7H, Ar-H), 4.46 (s, 2H, S-CH 2 -C). MS: [M] + at m/z Anal. Calcd. for C 16 H 10 Br 2 Cl 5 S: C, 37.27; H, 1.95;, 13.58: Found: C, 37.56; H, 1.76;, 13.69% 4-(2-hydroxybenzylideneamino)-5-(pyridin-4-yl)-3- thioacetylchlorid-1,2,4-triazole (3f) Yield 74% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 3445 (H), 3135 (aromatic CH), 1648 (C=), 1614 (C=C of aromatic ring), 1595 (=CH), 1492 (-), 1457 (C-), 683 (C-S-C). 1 HM (CDCl 3 ) δ in ppm: 12.21(s, 1H, H exchangeable with D 2 ), 8.86 (s, 1H, =CH), (m, 8H, Ar-H), 4.46 (s, 2H, S-CH 2 -C). MS: [M] + at m/z Anal. Calcd. for C 16 H 12 Cl 5 2 S: C,51.41; H, 3.24;, 18.73: Found: C, 51.75; H, 3.46;, 18.54% 4-(4-(dimethylamino)benzylideneamino)-5-(pyridin- 4-yl)-3-thioacetylchlorid-1,2,4-triazole (3g) Yield 73% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 3134 (aromatic CH), 1646 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 681 (C-S-C). 1 HM (CDCl 3 ) δ in ppm: 8.85 (s, 1H, =CH), (m, 8H, Ar-H), 4.47 (s, 2H, S-CH 2 -C), 3.06 (s, 6H, (CH 3 ) 2 ). MS: [M] + at m/z Anal. Calcd. for C 18 H 17 Cl 6 S: C, 53.93; H, 4.27;, 20.96: Found: C, 53.64; H, 4.58;, 20.58% General procedure for synthesis of (6-bromo-2- methyl-4-oxoquinazolin-3(4h)-yl)-2-(4- (substitutedbenzylideneamino)-5-(pyridin-4-yl)-3- thio)acetamido-1,2,4-triazoles (4a-4g) A mixture of 4-(substituted benzylideneamino)-5-(pyridin-4-yl)-4h-3-yl thioacetylchlorid- 1,2,4-triazoles (3a-3g) (0.05 mol) and 6-bromo-2-methyl-4-oxoquinazolin (0.05 mol) in ethanol (100 ml) was refluxed for 12 h. The solids thus obtained were filtered, dried and recrystallized from appropriate solvens to yielded compounds 4a- 4g. Yield (70%) (Petroleum ether); m.p C. I (KBr, ν max in cm -1 ): 3453 (H), 3136 (aromatic CH), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1614 (C=C of aromatic ring), 1593 (=CH), 1492 (-), 1455 (C-), 1224, (CH 3 ), 680 (C-S-C). 1 HM (CDCl 3 ) δ in ppm : (s, 1H, H exchangeable with D 2 ), 8.86 (s, 1H, =CH), (m, 10H, Ar-H), 6.95 (s, 1H, H exchangeable with D 2 ), 4.46 (s, 2H, S-CH 2 -C), 3.83 (s, 3H, CH 3 ), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 26 H 21 Br 8 4 S: C, 50.25; H, 3.41;, 18.03: Found: C, 50.36; H, 3.80;, 18.25% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2,4-dichlorobenzylideneamino)-5-(pyridin-3-yl)- 3-thio)acetamido-1,2,4-triazole (4b) Yield 68% (Acetone); m.p C. I (KBr, ν max in cm -1 ) : 3132 (aromatic CH), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1617 (C=C of aromatic ring), 1594 (=CH), 1491 (-), 1457 (C-), 761 (C-Cl), 681 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : 8.87 (s, 1H, =CH), (m, 10H, Ar-H), 6.96 (s, 1H, H exchangeable with D 2 ), 4.47 (s, 2H, S-CH 2 -C), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for 6
7 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL C 25 H 17 BrCl S: C, 46.60; H, 2.66;, 17.39: Found: C, 46.79; H, 2.85;, 17.69% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2,6-dichlorobenzylideneamino)-5-(pyridin-4-yl)- 3-thio)acetamido-1,2,4-triazole (4c) Yield 69% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 3135 (aromatic CH), 2886 (CH 3 ), 1683 (C=.amide), 1646 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 763 (C-Cl), 682 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : 8.85 (s, 1H, =CH), (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ),4.46 (s, 2H, S-CH 2 -C), 2.16 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 25 H 17 BrCl S: C, 46.60; H, 2.66;, 17.39: Found: C, 46.79; H, 2.85;, 17.69% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2,4-dibromobenzylideneamino)-5-(pyridin-4-yl)- 3-thio)acetamido-1,2,4-triazole (4d) Yield 65% (Petroleum ether); m.p C. I (KBr, ν max in cm -1 : 3132 (aromatic CH), 2884 (CH 3 ), 1682 (C=.amide), 1648 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C- ), 761 (C-Cl), 681 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : 8.86 (s, 1H, =CH), (m, 10H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 4.47(s, 2H, S-CH 2 -C), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 25 H 17 Br S: C, 40.95; H, 2.34;, 15.28: Found: C, 40.74; H, 2.65;, 15.47% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2,6-dibromobenzylideneamino)-5-(pyridin-4-yl)- 3-thio)acetamido-1,2,4-triazole (4e) Yield 63% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 3132 (aromatic CH), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 761 (C-Cl), 681 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : 8.87 (s, 1H, =CH), (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ), 4.49 (s, 2H, S-CH 2 -C), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 25 H 17 Br S: C, 40.95; H, 2.34;, 15.28: Found: C, 40.74; H, 2.65;, % -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-hyroxybenzylideneamino)-5-(pyridin-4-yl)-3- thio)acetamido-1,2,4-triazole (4f) Yield 62% (Ethanol); m.p.: C. I (KBr, ν max in cm -1 ): 3446 (H), 3135 (aromatic CH), 2887 (CH 3 ), 1683 (C=.amide), 1645 (C=), 1614 (C=C of aromatic ring), 1593 (=CH), 1493 (-), 1456 (C-), 680 (C-S-C), 610 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (s, 1H, H exchangeable with D 2 ), 9.57 (s, 1H, =CH), (m, 11H, Ar-H), 6.97 (s, 1H, H exchangeable with D 2 ), 4.46 (s, 2H, S- CH 2 -C), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 25 H 19 Br 8 3 S: C, 50.77; H, 3.24;, 18.95: Found: C, 50.94; H, 3.55;, 18.77% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(4(dimethylamino)benzylideneamino)-5-(pyridin- 4-yl)-3-thio)acetamido-1,2,4-triazole (4g) Yield 60% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 3134 (aromatic CH), 2885 (CH 3 ), 1683 (C=.amide), 1648 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 681 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : 8.88 (s, 1H, =CH), (m, 11H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 4.49 (s, 2H, S- CH 2 -C), 2.23 (s, 6H, (CH 3 ) 2 ), 2.19 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 24 Br 9 2 S: C, 52.43; H, 3.91;, 20.38: Found: C, 52.74; H, 3.75;, 20.47% 7
8 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(substitutedphenyl)-4-oxoazetidin-1- yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4-triazoles (5a-5g) A mixture of (6-bromo-2-methyl-4-oxoquinazolin- 3(4H)-yl)-2-(4-(substituted benzylideneamino)-5- (pyridin-4-yl)-4h-3-ylthio)acetamido-1,2,4-triazoles (4a-4g) (0.01 mole) in dry dioxan (10 ml) and triethylamine (0.005 mole) was taking in round bottom flask. The reactions were stirred on an ice bath and when temperature dropped below C, then choroacetylchloride (0.015 mole) was added dropwise with stirring and reaction mixtures were refluxed for 10 h and then kept a side for 50 h. Finally, the reaction mixtures were added to ice cold water to obtain the final product. It was dried and purified by recrystallization from appropriate solvents to furnish compounds 5a-5g. -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(4-hydroxy-3-methoxyphenyl)-4- oxoazetidin-1-yl)-5-(pyridin-4-yl)-3-thio)acetamido- 1,2,4-triazole (5a) Yield (69%) (Methanol); m.p C. I (KBr, ν max in cm -1 ): 3456 (H), 2887 (CH 3 ), 1685 (C=.amide), 1648 (C=), 1617 (C=C of aromatic ring), 1591 (=CH), 1495 (-), 1453 (C-), 680 (C-S-C), 760 (CH-Cl), 612 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (s, 1H, H exchangeable with D 2 ), (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.68 (d, 1H, -CH of oxoazetidine), 4.74 (d, 1H, CH-Cl of oxoazetidine), 4.46 (s, 2H, S-CH 2 -C), 3.39 (s, 3H, CH 3 ), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 28 H 22 BrCl 8 5 S: C, 48.18; H, 3.18;, 16.05: Found: C, 48.39; H, 3.25;, 16.35% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(2,4-dichlorophenyl)-4-oxoazetidin- 1-yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4- triazole (5b) Yield 77% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 761 (CH-Cl), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar- H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.68 (d,1h, -CH of oxoazetidine), 4.72 (d, 1H, CH-Cl of oxoazetidine), 4.45 (s, 2H, S-CH 2 -C), 2.19 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 18 BrCl S: C, 44.99; H, 2.52;, 15.55: Found: C, 44.87; H, 2.75;, 15.84% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(2,6-dichlorophenyl)-4-oxoazetidin- 1-yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4- triazole (5c) Yield 76% (Ethanol); m.p C. I (KBr, ν max in cm -1 ): 2883 (CH 3 ), 1685 (C=.amide), 1649 (C=), 1617 (C=C of aromatic ring), 1594 (=CH), 1495 (-), 1459 (C-), 763 (CH-Cl), 613 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar- H), 6.97 (s, 1H, H), 6.69 (d,1h, -CH of oxoazetidine), 4.75 (d,1h, CH-Cl of oxoazetidine), 4.47 (s, 2H, S-CH 2 -C), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 18 BrCl S: C, 44.99; H, 2.52;, 15.55: Found: C, 44.88; H, 2.74;, 15.83% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(2,4-dibromophenyl)-4-oxoazetidin- 1-yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4- triazole (5d) Yield 60% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 761 (CH-Cl), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar- 8
9 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL H), 6.99 (s, 1H, H exchangeable with D 2 ), 6.68 (d, 1H, -CH of oxoazetidine), 4.74 (d, 1H, CH-Cl of oxoazetidine), 4.46 (s, 2H, S-CH 2 -C), 2.16 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 18 Br 3 Cl 8 3 S: C, 40.05; H, 2.24;, 13.84: Found: C, 40.24; H, 2.55;, 13.56% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(2,6-dibromophenyl)-4-oxoazetidin- 1-yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4- triazole (5e) Yield 62% (Petroleum ether); m.p C. I (KBr, ν max in cm -1 ): 2889 (CH 3 ), 1683 (C=.amide), 1646 (C=), 1617 (C=C of aromatic ring), 1595 (=CH), 1496 (-), 1458 (C-), 764 (CH-Cl), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 6.69 (d,1h, -CH of oxoazetidine), 4.73 (d, 1H, CH-Cl of oxoazetidine), 4.47 (s, 2H, S-CH 2 -C), 2.16 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 18 Br 3 Cl 8 3 S: C, 40.05; H, 2.24;, 13.84: Found: C, 40.26; H, 2.47;, 13.59% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(2-hydroxyphenyl)-4-oxoazetidin-1- yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (5f) Yield 69% (Ethanol); m.p C. I (KBr, ν max in cm -1 ): 3481 (H), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1591 (=CH), 1492 (-), 1455 (C-), 761 (CH-Cl), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (s, 1H, H exchangeable with D 2 ), (m, 11H, Ar-H), 6.97(s, 1H, H exchangeable with D 2 ), 6.69 (d,1h, -CH of oxoazetidine), 4.74 (d,1h, CH-Cl of oxoazetidine), 4.45 (s, 2H, S-CH 2 - C), 2.19 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 20 BrCl 8 4 S: C, 48.55; H, 3.02;, 16.78: Found: C, 48.78; H, 3.25;, 16.97% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(3-chloro-2-(4-(dimethylamino)phenyl)-4- oxoazetidin-1-yl)-5-(pyridin-3-yl)-3-thio)acetamido- 1,2,4-triazole (5g) Yield 68% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1593(=CH), 1496 (-), 1458 (C-), 763 (CH-Cl), 614 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 11H, Ar- H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.67 (d,1h, -CH of oxoazetidine), 4.75 (d, 1H, CH-Cl of oxoazetidine), 4.47 (s, 2H, S-CH 2 -C), 2.24 (s, 6H, (CH 3 ) 2 ), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 29 H 25 BrCl 9 3 S: C, 50.12; H, 3.63;, 18.14: Found: C, 50.35; H, 3.96;, 18.45% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(substitutedphenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazoles (6a- 6g) To a ethanolic solution (60 ml) of (6-bromo-2- methyl-4-oxoquinazolin-3(4h)-yl)-2-(4-(substituted benzylideneamino)-5-(pyridin-4-yl)-4h-3- ylthio)acetamido-1,2,4-triazoles (4a-4g) (0.01 mol), thioglycolic acid (0.02 mol) was added in the presence of anhydrous zinc chloride. The reaction mixtures were refluxed for 15 h. The excess of solvent was distilled off and the reaction mixtures were poured into ice water, filtered, washed with water and recrystallized from appropriate solvents to yield compounds 6a-6g. Yield (64%) (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 3455 (H), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1622 (C= cyclized), 1591 (=CH), 1492 (-), 1455 (C-), 1227 (CH 3 ), 9
10 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL 761 (CH-Cl), 683 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm: (s,1h, H exchangeable with D 2 ), (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.69 (d,1h, -CH of oxothiazolidine), 3.73 (s, 2H, CH 2 of oxothiazoidine), 4.47 (s, 2H, S-CH 2 -C), 3.82 (s, 1H, CH 3 ), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 28 H 23 Br 8 5 S 2 : C, 48.35; H, 3.33;, 16.11:Found: C, 48.46; H, 3.70;, 16.32% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(2,4-dichlorophenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (6b) Yield 63% (Ethanol-water); m.p.: C. I (KBr, ν max in cm -1 ): 2889 (CH 3 ), 1686 (C=.amide), 1648 (C=), 1617 (C=C of aromatic ring), 1625(C= cyclized) 1595 (=CH), 1495 (- ), 1457 (C-), 763 (C-Cl), 685 (C-S-C), 610 (C- Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 6.70 (s, 1H, -CH of oxothiazolidine), 4.46 (s, 2H, S-CH 2 -), 3.74 (s, 2H, CH 2 of oxothiazolidine), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 19 BrCl S 2 : C, 45.14; H, 2.67;, 15.60: Found: C, 45.35; H, 2.86;, 15.35% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(2,6-dichlorophenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (6c) Yield 62% (Petroleum ether); m.p C. I (KBr, ν max in cm -1 ): 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1626 (C= cyclized), 1591 (=CH), 1492 (-), 1455 (C-), 761 (C-Cl), 683 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.71 (s,1h, - CH of oxothiazolidine), 4.47 (s, 2H, S-CH 2 -C), 3.75 (s, 2H, CH 2 of oxothiazolidine), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 19 BrCl S 2 : C, 45.14; H, 2.67;, 15.60: Found: C, 45.38; H, 2.89;, 15.45% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(2,4-dibromophenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (6d) Yield 60% (Methanol); m.p C. I (KBr, ν max in cm -1 ): 2890 (CH 3 ), 1686 (C=.amide), 1643 (C=), 1614 (C=C of aromatic ring), 1621 (C= cyclized), 1597 (=CH), 1490 (-), 1452 (C-), 685 (C-S-C), 613 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar-H), 6.98 (s, 1H, H exchangeable with D 2 ), 6.73 (s,1h, -CH of oxothiazolidine), 4.45 (s, 2H, S-CH 2 -C), 3.84 (s, 2H, CH 2 of oxothiazolidine), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 19 Br S 2 : C, 40.17; H, 2.37;, 13.88: Found: C, 40.35; H, 2.68;, 13.59% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(2,6-dibromophenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (6e) Yield 59% (Acetone); m.p C. I (KBr, ν max in cm -1 ): 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1623(C= cyclized), 1591 (=CH), 1492 (-), 1455 (C-), 683 (C-S-C), 611 (C-Br). 1 HM (CDCl 3 ) δ in ppm : (m, 10H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 6.70 (s, 1H, -CH of oxothiazolidine), 4.47 (s, 2H, S-CH 2 -C), 3.85 (s, 2H, CH 2 of oxothiazolidine), 2.17 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 19 Br S 2 : C, 40.17; H, 2.37;, 13.88: Found: C, 40.36; H, 2.67;, 13.58% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(2-hydroxyphenyl)-4-oxothiazolidin-3-yl)-5- (pyridin-4-yl)-3-thio)acetamido-1,2,4-triazole (6f) 10
11 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL Yield 61% (Ethanol); m.p C. I (KBr, ν max in cm -1 ): 3484 (H), 2885 (CH 3 ), 1680 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1625(C= cyclized), 1591 (=CH), 1493 (- ), 1455 (C-), 683 (C-S-C). 1 HM (CDCl 3 ) δ in ppm : (s,1h, H exchangeable with D 2 ), (m, 11H, Ar-H), 6.97 (s, 1H, H exchangeable with D 2 ), 6.72 (s,1h, -CH of oxothiazolidine), 4.46 (s, 2H, S-CH 2 -C), 3.83 (s, 2H, CH 2 of oxothiazolidine), 2.18 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 27 H 21 Br 8 4 S 2 : C, 48.73; H, 3.18;, 16.84: Found: C, 48.95; H, 3.37;, 16.54% -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2- (4-(2-(4-(dimethylamino)phenyl)-4-oxothiazolidin- 3-yl)-5-(pyridin-4-yl)-3-thio)acetamido-1,2,4- triazole (6g) Yield 59% (DMF-water); m.p C. I (KBr, ν max in cm -1 ): 2886 (CH 3 ), 1682 (C=.amide), 1645 (C=), 1615 (C=C of aromatic ring), 1620 (C= cyclized), 1591 (=CH), 1495 (-), 1457 (C-), 682 (C-S-C). 1 HM (CDCl 3 ) δ in ppm : (m, 11H, Ar-H), 6.99 (s, 1H, H exchangeable with D 2 ), 6.73 (s,1h,-ch of oxothiazolidine), 4.48(s, 2H, S-CH 2 -C), 3.84 (s, 2H, CH 2 of oxothiazolidine), 2.21 (s, 6H, (CH 3 ) 2 ), 2.14 (s, 3H, CH 3 ). MS: [M] + at m/z Anal. Calcd. for C 29 H 26 Br 9 3 S 2 : C, 50.29; H, 3.78;, 18.20: Found: C, 50.45; H, 3.99;, 18.46% ESULTS AD DISCUSSI All the synthesized compounds were screened for their antibacterial activities at a dose of 50 mg/kg i.p. and pharmacological data of these compounds have been reported in Table 1. Compound 1 exhibited zone of inhibition diameter of 6mm against S.aureus and 5mm against P. vulgaris 11 respectively. The characteristic feature of the compounds 2a-2g is the presence of azomethine (=CH-) linkage. Among compounds 2a-2g, compound 2a was devoid of antibacterial activity and compounds 2b, 2c 2d, 2e 2f and 2g have shown mild antibacterial activity. The 3-mercapto acetyl chloride of trazoles (3a 3g) associated with mild to moderate anti bacterial activity. These compounds exhibited i.e mm zone of inhibition against S. aureus, E. coli, P. vulgaris, K. pneumoniae. The addition of 6-bromo-2- methyl-4-oxoquinozoline with substituted triazoles yielded compounds 4a-4g. The compounds 4a-4g were found to possess moderate antibacterial activity. Compound 4b exhibited zone of inhibition 17mm against S. aureus, 15mm against P. vulgaris and 18mm against K. pneumoniae antibacterial activity. Compounds 4a-4g have shown better antibacterial activity than compounds 3a-3g. Cyclization of compounds 4a-4g into 5a-5g. Among azetidinones 5a-5g, compound 5b exhibited promising antibacterial activity. Compound 5b showed better antibacterial activity against S.aureus (21mm), E.coli (22mm), K. pneumoniae (20mm). Cyclization of compounds 4a-4g into 6a-6g. Among the compounds 6a-6g, compounds 6b and 6c showed better antibacterial activity than standard drug against S.aureus, E.coli and P.vulgaris. The compound 6e was found to exhibited equipotent antibacterial activity to that standard drugs. Compounds 6a, 6d, 6f and 6g showed good antibacterial activity. These compounds exhibited mm zone of inhibition against S. aureus, E. coli P. vulgaris, K. pneumoniae. The synthesized compounds were also tested for approximate lethal dose ALD 50 and were found to exhibit a higher value of ALD 50 i.e. more than 1000mg/kg i.p. except compound 6b, 6c which
12 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL exhibited ALD 50 of more than 2000mg/kg i.p. (maximum dose tested). As these compounds have Table 1a shown high value of ALD 50 thus indicating good safety margin. Antibacterial activity of the compounds: 4-amino-5-pyridin-3-mercapto-1,2,4-triazole (1),4-(4-hydroxy-3- methoxy benzylideneamino)-5-(pyridin-4-yl)-4h-3-mercapto-1,2,4-triazoles (2a-g). SH SH H 2 1 2(a-g) ALD 50 Compound Bacterial growth inhibition (diameter) Mg/kg i.p o. S. aureus E. coli P. vulgaris K. pneumoniae 1 6mm _ 5mm _ >1000 2a 4-H, 3-CH 3 >1000 2b 2,4-Cl 10mm 8mm 7mm _ >1000 2c 2,6-Cl 9mm _ 8mm 6mm >1000 2d 2,4-Br _ 7mm >
13 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL 2e 2,6-Br 5mm _ >1000 2f 2-H 6mm _ >1000 2g (CH 3 ) 2 6mm _ 7mm 5mm >1000 Ampicllin 20mm 18mm 18mm 14mm Gattifloxacin 25mm 22mm 20mm 21mm Table1b Antibacterial activity of the compounds: 4-(4-hydroxy-3-methoxy benzylideneamino)-5-(pyridin-4-yl)-4h-3- ylthioacetyl chloride-1,2,4-triazoles (3a-g), -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-(4- hydroxy-3-methoxybenzylidineamino)-5-(pyridin-4-yl)-4h-3-ylthio)acetamide-1,2,4-triazoles (4a-g). SCH 2 CCl CH SCH 2 CH CH Br (3a-g) (4a-g) ALD 50 Bacterial growth inhibition (diameter) Mg/kg i.p Compound o. S. aureus E. coli P. vulgaris K. pneumoniae 3a 4-H, 3-CH 3 10mm _ 8mm _ >
14 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL 3b 2,4-Cl 13mm 12mm >1000 3c 2,6-Cl _ 10mm >1000 3d 2,4-Br _ 11mm >1000 3e 2,6-Br 10mm _ 7mm _ >1000 3f 2-H 8mm _ 9mm 7mm >1000 3g (CH 3 ) 2 7mm _ 9mm _ >1000 4a 4-H, 3-CH 3 _ 12mm >1000 4b 2,4-Cl 17mm _ 15mm 18mm >1000 4c 2,6-Cl 15mm 14mm _ 13mm >1000 4d 2,4-Br _ 13mm 12mm _ >1000 4e 2,6-Br _ 12mm _ 11mm >1000 4f 2-H 11mm _ 10mm 9mm >1000 4g (CH 3 ) _ 11mm >1000 Ampicillin 20mm 18mm 18mm 14mm Gattifloxacin 25mm 22mm 20mm 21mm 14
15 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL Table1c Antibacterial activity of the compounds: -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-(3-chloro-2- (4-hydroxy-3-methoxyphenyl)-4-oxoazetidin-1-yl)-5-(pyridin-4-yl)-4H-3-ylthio)acetamide-1,2,4-triazoles (5ag), -(6-bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-(2-(4-hydroxy-3-methoxyphenyl)-4-oxothiazolidin- 3-yl)-5-(pyridin-4-yl)-4H-3-ylthio)acetamide-1,2,4-triazoles (6a-g). H C SCH 2 CH Br H C SCH 2 CH Br Cl S (5a-g) (6a-g) ALD 50 Bacterial growth inhibition (diameter) Mg/kg i.p Compound o. S. aureus E.coli P. vulgaris K. pneumoniae 5a 4-H, 3-CH 3-18mm 16mm - >1000 5b 2,4-Cl 21mm 22mm - 20mm >1000 5c 2,6-Cl 20mm 16mm - 17mm >1000 5d 2,4-Br 18mm 18mm 16mm - >1000 5e 2,6-Br 18mm - 15mm 17mm >
16 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL 5f 2-H 15mm 17mm - 12mm >1000 5g (CH 3 ) 2-16mm - 14mm >1000 6a 4-H, 3-CH 3 22mm - 20mm 21mm >1000 6b 2,4-Cl 26mm - 24mm - >2000 6c 2,6-Cl 27mm 23mm 21mm - >1000 6d 2,4-Br - 19mm - 20mm >1000 6e 2,6-Br 20mm - 20mm 21mm >1000 6f 2-H 21mm 18mm - - >1000 6g (CH 3 ) 2 18mm 19mm - - >1000 Ampicillin 20mm 18mm 18mm 14mm Gattifloxacin 25mm 22mm 20mm 21mm CCLUSIS While considering all the newly synthesized compounds of this series we may concluded that: 1. 2,4/2,6-di chlorophenyl substituted triazole derivatives showed more efficacy 2. Incorporation of azetidinones moieties are beneficial to antibacterial activities. 3 Compounds 6b and 6c are the most potent antibacterial compound of this series in comparision to used standard drugs viz. Ampicillin, Gattifloxacine. 4 Compounds 6a-6g containing thiazolidinones exhibited better antibacterial activity than rest of the compounds of this series. 16 EFEECE 1..A. Phillips, E.E. Udo, M.E. Abdel-Hamid,. Varghese; Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole)methyl oxazolidinones; Eur. J. Med. Chem., 44(B) (2009) S.D. Srivastava, T.. awat; Synthesis of new benzotriazole derivatives: antimicrobial and anticonvulsant agents; Indian J. Chem., 38B (1999) H.G. Jin, X.Y. Sun, K.Y. Chai, H.. Piao, S.Z. quan; Anticonvulsant and toxicity evaluation of some 7-alkoxy-4,5-dihydro-[1,2,4-]triazolo[4,3-
17 SYTHESIS AD ATIBACTEIAL ACTIVITY F SME EW PYIDIYL/QUIAZLIYL/AZETIDIYL/THIAZLIDIYL a]quinazolinone-1 (2H)-one; bioorg. Med. Chem., 20 (2006), Y. Dundar, B. Cakir, E. Kupeli, M.F. Sahin,. oyanalpan; Synthesis of some new 1- Acylthiosemicarbazides and 1,2,4-triazol-5- thiones and their analgesic and anti- Inflammatory activities; Turk J. Chem., 31 (2007) A. A.-M. Abdel-Aziz, H.I. El-Subbagh,T. Kunieda; Lewis acid-promoted transformation of 2-alkoxypyridines into 2-aminopyridines and their antibacterial activity. Part2: emarkably facile C- bond formation; Bioorganic & Med. Chem., 13 (2005) S.B. Holla, M.T. Padmaja, M.K. Shivananda, P.M. Akbarali; Synthesis and antibacterial activity of nitro furylvinyl quinazolinones. Indian J. Chem., 37B (1998) D.K. Shukla, S.D. Srivastava; Synthesis of some new 5-[2-{1,2,3-benzotriazol-1-yl-methyl}-1 - (4-substituted aryl-3-chloro-2-oxoazetidine)]- ameno-1,3,4-thiadiazoles:antifungal and antibacterial agents; Indian J. of Chem., 47B, (2008), S. Bhusare, B.A. Shinde, P.. Pawar P, B.Y. Vibhute; Synthesis and antimicrobial activity of heterocyclic schif bases, 4-thiazolidinones and 2-azetidinones; Indian J. Pharm. Sci., 3 (2004) Chuinckshank, J.P. Dugid,.H.A. Swain; Medical Microbiology, 2 (1975). 10. Q.E. Smith; Pharmacological Screening Tests Progressive, Medicinal Chemistry Butterworths, London, 1 (1960)
2 - chloro phenothiazine was prepared by the method of knoevenagal (loc. cit); (1914). 2-Chloro-10-chloroacetyl phenothiazine (1): To a solution of
103 104 SCHEME II SOME NEW SUBSTITUTED BENZYLIDENE AMINOTHIAZOL / OXAZOL PHENOTHIAZINES; SUBSTITUTED AZETIDINYL THIAZOL/ OXAZOL PHENOTHIAZINES HAVE BEEN SYNTHESIZED AS SHOWN IN SCHEME-II, INVOLVES THE
More informationSynthesis of some substituted azetidinonyl and thiazolidinonyl-1,3,4- thiadiazino[6,5-b]indoles as prospective antimicrobial agents
Indian Journal of Chemistry Vol. 45B, September 2006, pp. 2099-2104 Synthesis of some substituted azetidinonyl and thiazolidinonyl-1,3,4- thiadiazino[6,5-b]indoles as prospective antimicrobial agents Hemant
More informationSynthesis and Antimicrobial Evaluation of some 2-Azetidinone derivatives
International Journal of ChemTech Research CDE( USA): IJCRGG ISS : 0974-4290 Vol.1, o.2, pp 153-157, April-June 2009 Synthesis and Antimicrobial Evaluation of some 2-Azetidinone derivatives S.Jubie*, B.Gowramma,
More informationSynthesis of Some New 4,5-Substituted-4H-1,2,4-triazole-3-thiol Derivatives
Molecules 2004, 9, 204-212 molecules ISS 1420-3049 http://www.mdpi.org Synthesis of Some ew 4,5-Substituted-4-1,2,4-triazole-3-thiol Derivatives A. Cansız, M. Koparır * and A. Demirdağ Department of Chemistry,
More informationSYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES OF SOME 1-(NICOTINYLAMINO) -2 SUBSTITUTED AZETIDINE-4 -ONES AS POTENTIAL ANTIBACTERIAL AGENTS
Digest Journal of anomaterials and Biostructures Vol. 4, o.2, June 2009, p. 361 367 SYTHESIS, CHARACTERIZATI AD BILGICAL ACTIVITIES F SME 1-(ICTIYLAMI) -2 SUBSTITUTED AZETIDIE-4 -ES AS PTETIAL ATIBACTERIAL
More informationSYNTHESIS AND PHARMACOLOGICAL SCREENING OF N- SUBSTITUTED ANTHRANILIC ACID DERIVATIVES
慤 International Journal of Drug Development & Research April-June 2011 Vol. 3 Issue 2 ISS 0975-9344 Available online http://www.ijddr.in Covered in fficial Product of Elsevier, The etherlands 2010 IJDDR
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationInternational Journal of Pharma and Bio Sciences V1(2)2010 SY THESES A D BIOLOGICAL ACTIVITY OF SOME 3, 5-DRIARYL-4H-1, 2, 4-TRIAZOLE DERIVATIVES
RAM JA AM SI GH *1 A D DHARME DRA KUMAR SI GH 2 1 Quality Control Laboratory, Indian Oil Corporation Limited, Panipat, Haryana-132140 (India) 1, 2 Synthetic Research Laboratory, Department of Chemistry,
More informationSynthesis of Some 4-Thiazolidinone Derivatives as Antitubercular Agents
Journal of ciences, Islamic Republic of Iran 15(2): 143-148 (2004) University of Tehran, I 1016-1104 hort Communication ynthesis of ome 4-Thiazolidinone Derivatives as Antitubercular Agents H.H. Parekh,
More informationA Novel Synthesis of Arylpyrrolo[1,2-a]pyrazinone Derivatives
Molecules 2004, 9, 574-582 molecules ISS 1420-049 http://www.mdpi.org A ovel Synthesis of ylpyrrolo[1,2-a]pyrazinone Derivatives Fei Wang*, Jiawei Wang and Shoufang Zhang School of Pharmaceutical Engineering,
More informationSyntheses and antitumor activity of some 1,2,4 triazine derivatives
ISS: 2319-8753 (An IS 3297: 2007 Certified rganization) Syntheses and antitumor activity of some 1,2,4 triazine derivatives Heba A.El-Hady* 1,2 and Sahar S. El Sakka 3 Department of Chemistry, Faculty
More informationRegioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
More informationSupporting Information. Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
Supporting Information Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition Shan Xu, Juyou Lu and Hua Fu* Key Laboratory of Bioorganic Phosphorus Chemistry and
More informationISSN: X Available Online through Research Article
ISSN: 0975-766X Available Online through Research Article www.ijptonline.com PHARMACOLOGICAL SCREENING OF NEW ISATIN-3-[N 2 -HETERYL-2-THIOACETYL] HYDRAZONES M.Ajitha 1 *, K.Rajnarayana 2, M.Sarangapani
More informationInternational Journal of ChemTech Research CODEN (USA): IJCRGG ISSN: Vol.8, No.4, pp , 2015
International Journal of ChemTech esearch CDE (USA): IJCGG ISS: 0974-4290 Vol.8, o.4, pp 2096-2100, 2015 Synthesis and Antimicrobial Activity of 2-amino-4- (substitutedphenyl)-6-{4-[3-chloro-2-(4-hydroxyphenyl)-4-
More informationANTIMICROBIAL SCREENING OF N-[(2-SUBSTITUTED PHENYL)-4-OXO-1,3-THIAZOLIDINE 3- YL]ISONICOTINAMIDES
ATIMICROBIAL SCREEIG OF -[(2-SUBSTITUTED PHEYL)-4-OXO-1,3-THIAZOLIDIE 3- YL]ISOICOTIAMIDES V. H. Bhaskar 1 *, M. Kumar 2 and B. Sangameswaran 2 1 Sri Ramnath Singh Institute of Pharmaceutical Sciences
More informationSynthesis and Anti Convulsant Activity of Novel Oxadiazole Substituted Phenothiazine Derivatives
ynthesis and Anti Convulsant Activity of ovel xadiazole ubstituted Phenothiazine Derivatives Dighe 1*, Bankar AA 1, Musmade D 2 and irmal A 3 1 Department of Pharmaceutical Chemistry, Pravara ural College
More informationSUBMISSION OF THE FINAL REPORT OF THE WORK DONE ON THE PROJECT
SUBMISSION OF THE FINAL REPORT OF THE WORK DONE ON THE PROJECT NAME OF THE PRINCIPAL INVESTIGATOR : Dr.V.M.Barot, NAME AND ADDRESS OF THE INSTITUTION : Smt.S.M.Panchal Science College, -383215,Gujarat
More informationParesh S. More*, Santosh G. Singh. Department of Chemistry, KET S V.G Vaze College, Mulund(E), Mumbai , Maharashtra, India
International Letters of Chemistry, Physics and Astronomy Online: 20150224 ISSN: 22993843, Vol. 47, pp 4955 doi:10.18052/www.scipress.com/ilcpa.47.49 2015 SciPress Ltd., Switzerland Synthesis and characterization
More informationSynthesis and biological activities of some 3,5-disubstituted-Δ²-pyrazoline derivatives
Oriental Journal of Chemistry Vol. 24(2), 607-612 (2008) Synthesis and biological activities of some 3,5-disubstituted-Δ²-pyrazoline derivatives SADAF J.GILANI, SUROOR A. KHAN*, OZAIR ALAM and HARISH KUMAR
More informationJournal of Chemical and Pharmaceutical Research
Available on line www.jocpr.com Journal of Chemical and Pharmaceutical Research J. Chem. Pharm. Res., 2010, 2(2): 50-56 ISS o: 0975-7384 Antimicrobial and antifungal screening of indanone acetic acid derivatives
More informationSYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 2,4,6-TRISUBSTITUTED PYRIMIDINES
INTERNATIONAL JOURNAL OF RESEARCH IN PHARMACY AND CHEMISTRY Available online at www.ijrpc.com Research Article SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 2,4,6-TRISUBSTITUTED PYRIMIDINES B. Anupama
More informationAn Efficient Synthesis of Bio Active Azetidinones and Thiazolidinones of 3-METHYL-1-PHENYL-1H- PYRAZOL-5-OL
International Journal of Scientific and Research Publications, Volume 2, Issue 6, June 2012 1 ISS 2250-3153 An Efficient Synthesis of Bio Active Azetidinones and Thiazolidinones of 3-METHYL-1-PHEYL-1H-
More informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
More informationIssue in Honor of Prof. Edmund Lukevics ARKIVOC 2006 (v) 86-91
Issue in onor of Prof. Edmund Lukevics ARKIVC 2006 (v) 86-91 Polycyclic heterocycles with acidic - groups VIII 1 The synthesis of some binuclear - acids with free rotary 1,2,4- triazole, 6-azauracil and
More informationLewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS) Dinneswara Reddy Guda, Hyeon Mo Cho, Myong
More informationReceived 05 March, 2010; received in revised form 20 April, 2010; accepted 20 May, 2010
ISS: 0975-8232 IJPS (2010), Vol. 1, Issue 6 (esearch Article) eceived 05 March, 2010; received in revised form 20 April, 2010; accepted 20 May, 2010 SYTHESIS OF 3- (1 BEZYL - 1H - BEZO [D] IMIDAZOL 2 -
More informationSupporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
More informationThe synthesis of condensed imidazoles II. A simple synthesis of some 1,5-diaryl-3-[2-(naphtho[2,3-d]imidazol-2-yl)]formazans and its derivatives 1
The synthesis of condensed imidazoles II. A simple synthesis of some 1,5-diaryl-3-[2-(naphtho[2,3-d]imidazol-2-yl)]formazans and its derivatives 1 Iveta Fryšová *, Jan Slouka, and Jan laváč Department
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationThe First Au-Nanoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine
Supporting information of The First Au-anoparticles Catalyzed Green Synthesis of Propargylamines Via Three-Component Coupling Reaction of Aldehyde, Alkyne And Amine Mazaahir Kidwai a *, Vikas Bansal a,
More informationNaoya Takahashi, Keiya Hirota and Yoshitaka Saga* Supplementary material
Supplementary material Facile transformation of the five-membered exocyclic E-ring in 13 2 -demethoxycarbonyl chlorophyll derivatives by molecular oxygen with titanium oxide in the dark Naoya Takahashi,
More informationJulee P. Soni, Dhrubo Jyoti Sen and Kamal M. Modh ABSTRACT INTRODUCTION
ISS: 2231-3354 eceived: 28-05-2011 evised : 07-06-2011 Accepted: 09-06-2011 Structure activity relationship studies of synthesised pyrazolone derivatives of imidazole, benzimidazole and benztriazole moiety
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationSYNTHESIS OF 6-CHLOROFLAVONE FROM 4-CHLOROPHENOL AND THEIR BIOCIDAL ACTIVITY
Int. J. Chem. Sci.: 14(4), 2016, 2003-2011 ISSN 0972-768X www.sadgurupublications.com SYNTHESIS F 6-CHLRFLAVNE FRM 4-CHLRPHENL AND THEIR BICIDAL ACTIVITY VAISHALI B. ADHAU * Department of Chemistry, Vidarbha
More informationSUPPORTING INFORMATION. Studies on antimicrobial evaluation of some 1-((1-(1H-benzo[d]imidazol-2-
SUPPORTIG IFORMATIO Studies on antimicrobial evaluation of some 1-((1-(1H-benzo[d]imidazol-2- yl)ethylidene)amino)-6-((arylidene)amino)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5- dicarbonitriles C Desai*,
More informationSupporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
More informationSynthesis and Antimicrobial Activity of Azetidin- 2-one Containing Acetyl Pyrazoline Derivatives
International Journal of ChemTech esearch CDE( USA): IJCGG ISS : 0974-4290 Vol.4, o.3, pp 933-938, July-Sept 2012 Synthesis and Antimicrobial Activity of Azetidin- 2-one Containing Acetyl Pyrazoline Derivatives
More informationVol-3, Issue-3, July-2012 ISSN: Panda et al
PHARMA SCIENCE MONITOR AN INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES SYNTHESIS OF SOME ANTIBACTERIAL, ANALGESIC AND ANTI- INFLAMMATORY AGENTS CONTAINING ISATIN NUCLEUS Jnyanaranjan Panda Post Graduate
More informationAvailable Online through
ISSN: 0975-766X CODEN: IJPTFI Available Online through Research Article www.ijptonline.com SYNTHESIS, ANTIMICROBIAL AND WOUND HEALING ACTIVITIES OF DIPHENYL QUINOXALINE DERIVATIVES M.Geethavani 1*, Dr.
More informationRSC Advances.
This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationSynthesis and Biological activity of some Novel 1, 3, 4-Thiadiazole derivatives
International Journal of ChemTech Research CODE (UA): IJCRGG I : 0974-4290 Vol.4, o.1, pp 74-78, Jan-Mar 2012 ynthesis and Biological activity of some ovel 1, 3, 4-Thiadiazole derivatives M. arayana Babu*,
More informationVora et al., IJPSR, 2012; Vol. 3(1): ISSN:
Vora et al., IJPS, 2012; Vol. 3(1): 162-167 ISS: 097-8232 IJPS (2012), Vol. 3, Issue 1 (esearch Article) eceived on 30 August, 2011; received in revised form 18 ctober, 2011; accepted 22 December, 2011
More informationTetramethyl guanidine (TMG) catalyzed synthesis of novel α-amino phosphonates by one-pot reaction
RIGINAL ARTICLE rg. Commun.3:3 (2010) 39-44 Tetramethyl guanidine (TMG) catalyzed synthesis of novel α-amino phosphonates by one-pot reaction M. Veera Narayana Reddy, S. Annar, A. Bala Krishna, G. Chandra
More informationCopper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of. Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis
Copper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis of Fully Substituted Pyrazoles Shirin Safaei, Iraj Mohammadpoor-Baltork,*
More informationSynthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice
Supporting Information Rec. Nat. Prod. 9:4 (2015) 561-566 Synthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice Anita Mahapatra 1*, Purvi Shah 1, Mehul Jivrajani
More informationASIAN JOURNAL OF CHEMISTRY
Asian Journal of Chemistry; Vol. 29, o. 9 (2017), 2084-2090 ASIA JUAL F CEMISTY https://doi.org/10.14233/ajchem.2017.20832 Synthesis and Characterization of Antitubercular Triazine-Chalcone ybrid Molecules
More informationDesign, Synthesis and Evaluation of Biological activity of certain Novel Triazole schiff bases
Research Article Design, Synthesis and Evaluation of Biological activity of certain Novel Triazole schiff bases Bhagyalakshmi N 1, Udupi RH 2* and Niranjan MS 1 1 Govt. college of pharmacy, Bangalore.
More informationp-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationElectronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
More information3016 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid
6 Oxidation of ricinoleic acid (from castor oil) with KMnO 4 to azelaic acid CH -(CH ) OH (CH ) -COOH KMnO 4 /KOH HOOC-(CH ) -COOH C H 4 O (.) KMnO 4 KOH (.) (6.) C H 6 O 4 (.) Classification Reaction
More information1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 7 Supporting Information for,5-electrocyclization of conjugated azomethine ylides
More informationEvaluation of Biological Activity (In-Vitro) of Some 2-Phenyl Oxazoline Derivatives
Human Journals Research Article April 2016 Vol.:6, Issue:1 All rights are reserved by V.Niraimathi et al. Evaluation of Biological Activity (In-Vitro) of Some 2-Phenyl Oxazoline Derivatives Keywords: Antimicrobial
More informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
More informationSupporting Information. An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization
Supporting Information An Efficient Synthesis of Optically Active Physostigmine from Tryptophan via Alkylative Cyclization Michiaki, Kawahara, Atsushi Nishida, Masako Nakagawa* Faculty of Pharmaceutical
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More informationSupporting information for
Supporting information for A Coordination Gelator that Shows a Reversible Chromatic Change and a Sol-Gel Phase Transition Behavior upon xidative / Reductive Stimuli Shin-ichiro Kawano, orifumi Fujita,
More informationSynthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor
upplementary Material for rganic & Biomolecular Chemistry ynthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor Lyn. Jones* Amy Randall, scar Barba
More informationSupporting Information
Supporting Information Synthesis of Pyrido-fused Quinazolinone Derivatives via Copper-catalyzed Domino Reaction Meilin Liu, Miaomiao Shu, Chaochao Yao, Guodong Yin,* Dunjia Wang, and Jinkun Huang* Hubei
More informationMasatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationGeneral Papers ARKIVOC 2008 (xvii)
General Papers AKIVC 2008 (xvii) 117-121 Arylhydrazonals as aldehyde components in Baylis-Hillman reaction: synthesis of 5-hydroxy-2,3,4,5-tetrahydropyridazine-4- carbonitrile and 6,7,8,8a-tetrahydrocinnolin-5(1H)-one
More informationResearch Article. Synthesis and biological evaluation of some novel heterocyclic compounds as protein tyrosine phosphatase (PTP-1B) Inhibitor
Available online www.jocpr.com Journal of Chemical and Pharmaceutical esearch, 2015, 7(10):509-517 esearch Article I : 0975-7384 CDE(UA) : JCPC5 ynthesis and biological evaluation of some novel heterocyclic
More informationCDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines
Supporting information: CDI Mediated Monoacylation of Symmetrical Diamines and Selective Acylation of Primary Amines of Unsymmetrical Diamines Sanjeev K. Verma*, Ramarao Ghorpade, Ajay Pratap and M. P.
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Gold Catalysis: The Phenol Synthesis in the Presence of Functional Groups A. Stephen K. Hashmi, Jan P. Weyrauch,
More informationSupporting Information
Palladium-Catalyzed Cascade Oxidantion/sp 2 C-H Acylation of Azoarenes with Aryl Methanes Feng Xiong, a Cheng Qian, b Dongen Lin, b Wei Zeng b,* and Xiaoxia Lu a,* a Chengdu Institute of Biology,CAS, Chengdu
More informationβ-sitosterol-3-o-β-d-xylopyranosyl (1 4)-O-β-D- GLUCOPYRANOSIDE FROM THE SEEDS OF ZANTHOXYLUM HEMILTONIANUM WALL
Int. J. Chem. Sci.: 11(2), 201, 111-116 ISSN 0972-768X www.sadgurupublications.com β-sitsterl---β-d-xylpyransyl (1 4)--β-D- GLUCPYRANSIDE FRM TE SEEDS F ZANTXYLUM EMILTNIANUM WALL SANDYA RAJPT * Department
More informationWITHDRAWN. See: WITHDRAWN
Molecules 2007, 12, 673-678 WITHDRAW. See: http://www.mdpi.org/molecules/papers/12092160.pdf molecules ull Paper ISS 1420-3049 http://www.mdpi.org Synthesis of Gefitinib from Methyl 3-Hydroxy-4-methoxy-benzoate
More informationResearch Article Synthesis of Some Newer Derivatives of Thiadiazole as Anti-Inflammatory and Analgesic Agents
ITEATIOAL JOUAL OF PAMAEUTIAL AD EMIAL IEE I: 2277 5005 esearch Article ynthesis of ome ewer Derivatives of Thiadiazole as Anti-Inflammatory and Analgesic Agents Indu ingh Department of hemistry, JV ollege
More informationSyntheses of aromatic aldehyde imine derivatives of 2-thiobenzyl-1,3,4-thiadiazole and evaluation of their anticonvulsant activity
Indian Journal of Chemistry Vol. 49B, February 2010, pp. 241-246 ote yntheses of aromatic aldehyde imine derivatives of 2-thiobenzyl-1,3,4-thiadiazole and evaluation of their anticonvulsant activity Bahar
More informationSupporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
More informationInternational Journal Of Scientific Research And Education Volume 3 Issue 6 Pages June-2015 ISSN (e): Website:
International Journal f Scientific Research And Education Volume 3 Issue 6 Pages-3622-3627 June-2015 ISS (e): 2321-7545 Website: http://ijsae.in Synthesis of Some Tri-Substituted Imidazoles From Benzil
More informationSynthesis and Biological Significance of b -D-Glucuronides
International Journal of ChemTech esearch CDE( USA): IJCGG ISS : 0974-4290 Vol.4, o.2, pp 655-661, April-June 2012 Synthesis and Biological Significance of b -D-Glucuronides ajendra Krushnaji Wanare Department
More informationThermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein
Supplementary Methods Thermal shift assays Thermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein unfolding was examined by monitoring the fluorescence of ANS (1-anilinonaphthalene-8-
More informationA Hierarchy of Aryloxide Deprotection by Boron Tribromide. Supporting Information
A Hierarchy of Aryloxide Deprotection by Boron Tribromide Sreenivas Punna, Stéphane Meunier and M. G. Finn* Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute,
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Supporting Information An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines
More informationISSN: A one-pot multi component synthesis of triazolopyrimidines
Trade Science Inc. ISS: 0974-751 Volume 8 Issue 11 rganic CEMISTRY CAIJ, 8(11 2012 [419-423] A one-pot multi component synthesis of triazolopyrimidines Ranjit Pada, aresh Ram*, Ram andaniya, Dipti Dodiya,
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationHighly efficient hydrazination of conjugated nitroalkenes via imidazole or DMAP mediated Morita-Baylis-Hillman reaction
Experimental Data and ptimization Tables For Highly efficient hydrazination of conjugated nitroalkenes via imidazole or DMAP mediated Morita-Baylis-Hillman reaction M. Dadwal, S. M. Mobin, I... amboothiri
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2009 ISSN X SUPPORTING INFORMATION
Eur. J. rg. Chem. 2009 WILEY-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2009 ISS 1434 193X SUPPRTIG IFRMATI Title: ew GM1 Ganglioside Derivatives for Selective Single and Double Labelling of the atural
More informationSupporting Information. Use of Potassium. -Trifluoroborato Amides in Suzuki-Miyaura. Cross-Coupling Reactions
Supporting Information Use of Potassium -Trifluoroborato Amides in Suzuki-Miyaura Cross-Coupling Reactions Gary A. Molander* and Ludivine Jean-Gérard Roy and Diana Vagelos Laboratories, Department of Chemistry,
More informationAn efficient synthesis, characterization and anti-bacterial activity of pyrimidine bearing 1,3,4-thiadiazole derivatives
Indian Journal of Chemistry Vol. 54B, March 2015, pp. 406-411 An efficient synthesis, characterization and anti-bacterial activity of pyrimidine bearing 1,3,4-thiadiazole derivatives Andrews B* a,b & Mansur
More informationAsian Journal of Pharmaceutical Analysis and Medicinal Chemistry Journal home page:
Research Article CDE: AJPAD7 ISS: 2321-0923 Asian Journal of Pharmaceutical Analysis and Medicinal Chemistry Journal home page: www.ajpamc.com SYTHESIS, CHARACTERIZATI AD ATIMICRBIAL EVALUATI F DIHYDR-5-SUBSTITUTED-2-THIXPYRIMIDIES
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationFluorescent probes for detecting monoamine oxidase activity and cell imaging
Fluorescent probes for detecting monoamine oxidase activity and cell imaging Xuefeng Li, Huatang Zhang, Yusheng Xie, Yi Hu, Hongyan Sun *, Qing Zhu * Supporting Information Table of Contents 1. General
More informationA pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state
A pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state Mingguang Pan, Min Xue* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Fax:
More informationSynthesis, characterization and antibacterial evaluation of novel 2- pyrazoline derivatives
Available online at www.derpharmachemica.com Scholars Research Library Der Pharma Chemica, 2012, 4 (1):33-38 (http://derpharmachemica.com/archive.html) ISS: 0975-413X CDE (USA): PCHHAX Synthesis, characterization
More informationUse of degradable cationic surfactants with cleavable linkages for enhancing the. chemiluminescence of acridinium ester labels. Supplementary Material
Use of degradable cationic surfactants with cleavable linkages for enhancing the chemiluminescence of acridinium ester labels Supplementary Material Anand atrajan*and David Wen Siemens Healthcare Diagnostics
More informationPt IV azido complexes undergo copper-free click reactions with alkynes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 208 Pt IV azido complexes undergo copper-free click reactions with alkynes Electronic Supplementary
More informationmm C3a. 1 mm C3a Time (s) C5a. C3a. Blank. 10 mm Time (s) Time (s)
125 I-C5a (cpm) Fluorescnece Em 520nm a 4000 3000 2000 1000 c 0 5000 4000 3000 2000 Blank C5a C3a 6 0.3 mm C3a 7 9 10 11 12 13 15 16 0.3 mm C5a 0 300 600 900 1200 Time (s) 17 Fluorescnece Em 520nm Fluorescnece
More informationChristophe Lincheneau, Bernard Jean-Denis and Thorfinnur Gunnlaugsson* Electronic Supplementary Information
Self-assembly formation of mechanically interlocked [2]- and [3]catenanes using lanthanide ion [Eu(III)] templation and ring closing metathesis reactions Christophe Lincheneau, Bernard Jean-Denis and Thorfinnur
More informationCHAPTER - 3. SYNTHESIS OF INDENO[1,2-d]PYRIMIDINE-2-THIONES AND EXPERIMENTAL. plates and spots were located by iodine vapours. Infra red spectra were
CAPTER - 3 YTEI OF IDEO[1,2-d]PYRIMIDIE-2-TIOE AD TEIR ALKYL/ARALKYL DERIVATIVE EXPERIMETAL Melting points were determined in open end capillaries and are uncorrected. Compounds were checked for their
More informationSYNTHESIS OF NOVEL BENZIMIDAZOLE DERIVATIVES POTENT ANTIMICROBIAL AGENT.
http://www.rasayanjournal.com Vol.2, o.1 (2009), 186-190 ISS: 0974-1496 CODE: RJCABP SYTESIS OF OVEL BEZIMIDAZOLE DERIVATIVES AS POTET ATIMICROBIAL AGET. Bhushan Baviskar* 1, Bhagyesh Baviskar 2, Suvarna
More informationSUPPORTING INFORMATION
SUPPORTING INFORMATION Synthesis and Preliminary Pharmacological Evaluation of Aryl Dithiolethiones with Cyclooxygenase-2 Selective Inhibitory Activity and Hydrogen-Sulfide-Releasing Properties Shannon
More informationSUPPLEMENTAL FIGURE 1 Structures and IC50 values of compounds 13 32
SUPPLEMETAL FIGURE 1 Structures and IC50 values of compounds 13 32 THE JURAL F UCLEAR MEDICIE Vol. 53 o. 11 ovember 2012 Synthesis of [ 19 F]1 ([ 19 F]--(2-{4-[5-(benzyloxy)pyridin-2-yl]piperazin-1-yl}-2-oxoethyl)-
More informationScholars Research Library
Available online at www.scholarsresearchlibrary.com Scholars Research Library Archives of Applied Science Research, 2010, 2 (2): 72-78 (http://scholarsresearchlibrary.com/archive.html) ISSN 0975-508X CODEN
More informationJournal of Chemical and Pharmaceutical Research
Available on line www.jocpr.com Journal of Chemical and Pharmaceutical Research I o: 0975-7384 CDE(UA): JCPRC5 J. Chem. Pharm. Res., 2011, 3(1):402-413 A ew Approach for the ynthesis of ome ovel ulphur
More informationScreening of Antimicrobials of some Medicinal Plants by TLC Bioautography
Screening of Antimicrobials of some Medicinal Plants by TLC Bioautography Middha Himanshu 1* and Parihar Pradeep 2 1Department of Microbiology, DTM College of Biosciences, Bikaner, Rajasthan 2 Lovely Professional
More informationSupplemental Information. Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates
Supplemental Information Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates Kathryn A. Berchtold a, Jun Nie b, Jeffrey W. Stansbury c, d, and Christopher N. Bowman c, d, a Materials Science
More information