Research & Reviews: Journal of Medicinal & Organic Chemistry

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1 Research & Reviews: Journal of Medicinal & Organic Chemistry Synthesis, Characterization and Antimicrobial Evaluation of Novel Organo Phospho Carbamates Containing Imidazole Ureas/Carboxamides Esther Rani V *, Marasakatla Rani 2 and Ravindranath LK 2 Department of Chemistry, S K University, Anantapur, AP, India 2 Biomedical Engineering, Osmania University, Hyderabad, Telangana, India Research Article Received date: 20/0/ 205 Accepted date: 23// 205 Published date: 05/0/206 *For Correspondence Esther Rani V, Department of Chemistry, Sri Krishnadevaraya University, Anantapur, AP, India vesther9@gmailcom Keywords: Imidazole; Phospho ureas; Carboxamides; Antibacterial; Antifungal activity ABSTRACT The novel Organo Phospho Carbamates containing imidazole ureas/ Carboxamides derivatives are an important class of organophosphorus heterocycles, having potential biological importance due to their unique features The conversion of acid azide to urethanes (carbamates through isocyanate involves Curtius rearrangement is an important synthetic method for the preparation of substituted ureido/carboxamide carbamates They have multifacted applications as important pharmacophores in agriculture, pharmaceuticals, chemical synthesis and diverse other potential biological areas The compounds electron withdrawing group at position 4 of ureido/carboxamide carbamates increased the activity against bacteria and fungus INTRODUCTION The high therapeutic properties of the imidazole related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents Imidazole drugs have broadened scope in remedying various dispositions in clinical medicines Numerous methods for the synthesis of imidazole and also their various structure reactions offer enormous scope in the field of medicinal chemistry Literature survey revealed that imidazole and its derivative are reported to have, antianthelmintic activity [], cardiovascular activity [2], analgesic and anti-inflammatory activity [3], anti-neoplastic activity [4], anti-fungal activity [5], enzyme inhibition activity, anti-filarial agent, anti-viral activity and anti-ulcer activity [6] The chemistry of phosphorus heterocyclic compounds containing nitrogen plays an important role in the development of new pharmaceutical materials with novel properties The chemistry of organophosphorus compounds and their derivatives were found to be the highlight of study in lead compound discovery and biological screening and study of their various biological activities such as anti-bacterial [7], herbicides, insecticides, pesticides [8], anti-fungal agents [9], anti-hiv [0], anti-cancer [], anti-viral and anti-inflammatory [2] including its application in the field of Agriculture, medicine and industry [3] A good deal of importance was given to synthesized Imidazole possessing carbamate moiety besides dioxaphosphepino ureas/carboxamides screening for possible biological and pharmacological activities Solvents, reagents and conditions (-2 Isobutyl chloroformate, triethylamine stirred for 30 minutes and add Na stirred for 20 minutes at 0 C (2-4 The reaction mixture was refluxed for 6 hrs (4(a-d-5(a-d Dry acetone, PTA, the reaction mixture stirred at RT, under nitrogen atm for hr (Step- and 2 [4] Dry toluene, triethylamine, THF addition at 5 C, the reaction mixture slowly raised at RT, stirred for 2 hrs and heated at C and stirred for 4 hrs EXPERIMENTAL SECTION 2-(6,6-dimethyl-4,8-dihydro- H-[,3]dioxepino[5,6-d]imidazole--yl acetyl azide (2 Yield 70% m p: C IR (KBr: 2940 and 2895 (CH 2 and CH 3 of aliphatic-ch, (, 395 (C (CH 3 2 stretching Issue June, 206

2 vibration, 670, 40 and 285 cm - corresponding stretching vibrations of C=O, C-N of azide and C-O respectively H-NMR (400 MHz, DMSO-d 6 27 (s, 6H, two geminial CH 3 groups, 457 (s, 4H, two CH 2 groups of acetals, 484 (s, 2H, N-CH 2 -CO, 757 (s, H of imidazole ring AnalCalcdFor C 0 H 3 O 3 C: 478, H: 522 and N: 2787% Found: C: 470, H: 472 and N 2727% Cyclohexyl ((6,6-dimethyl-4,8-dihydro- H-[,3] dioxepino [5,6-d]imidazol--yl methyl carbamate (4a Yield 68% m p: C IR (KBr: (N-H, 3050 (stretching of Ar-H, 2940 and 2895 (aliphatic C-H stretching, 75 (C=O, 68 (C=N, 46 (C-N, 395 (C (CH 3 2 bending vibration and 320 cm - (C-O respectively H-NMR (400 MHz, DMSO-d 6 27 (s, 6H two geminial CH 3 groups, (m, 0H, CH 2 of cyclohexyl, 39 (m, H, O-CH of cyclohexyl 457 (s, 4H two CH 2 groups of acetals, 540 (d, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO AnalCalcdFor C 6 H 25 C: 5942, H: 779 and N 299% Found: C : 5862, H: 729 and N: 239% Tetrahydro-2H-pyran-4-yl ((6,6-dimethyl-4,8-dihydro- H-[,3] dioxepino [5,6-d]imidazol--yl methyl carbamate (4b Yield 68% m p: C IR (KBr: (N-H, 3052 (stretching of Ar-H, 2940 and 2895 (aliphatic C-H stretching, 75 (C=O, 620 (C=N, 48 (C-N, 395 (C (CH 3 2 bending vibration and 324 cm - (C-O respectively H-NMR (400 MHz, DMSO-d 6 27 (s, 6H two geminial CH 3 groups, (m, 0H, CH 2 of cyclohexyl, 39 (m, H, O-CH of cyclohexyl 457 (s, 4H two CH 2 groups of acetals, 540 (d, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO AnalCalcdFor C 5 H 23 O 5 C: 5537, H: 73 and N: 29% Found: C: 5457, H: 663 and N 23% Tetrahydro-2H-thiopyran-4-yl ((6,6-trimethyl-4,8-dihydro- H-[,3] dioxepino [5,6-d] imidazol--yl methyl carbamate (4c Yield 68% m p: C IR (KBr: (N-H, 3052 (stretching of Ar-H, 2940 and 2895 (aliphatic C-H stretching, 75 (C=O, 620 (C=N, 48 (C-N, 395 (C(CH 3 2 bending vibration, 324 (C-O and 75 cm - (C-S respectively H-NMR (400 MHz, DMSO-d 6 27 (s, 6H two geminial CH 3 groups, (m, 0H, CH 2 of cyclohexyl, 39 (m, H, O-CH of cyclohexyl 457 (s, 4H two CH 2 groups of acetals, 540 (d, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO AnalCalcdFor C 5 H 23 S C: 5277, H: 679, N: 23 and S: 939% Found: C: 597, H: 629, N: 7 and S: 99% Perfluorophenyl ((6,6-dimethyl-4,8-dihydro- H-[,3] dioxepino[5,6-d]imidazol--yl methyl carbamate (4d Yield 70%m p: C IR (KBr: (N-H, 3052 (stretching of Ar-H, 2940 and 2895 (aliphatic C-H stretching, 75 (C=O, 620 (C=N, 420 (C-N, 395 (C (CH 3 2 bending vibration, 326 (C-O and 00 cm - (C-F respectively H-NMR (400 MHz, DMSO-d 6 27(s, 6H two geminial CH 3 groups, 457 (s, 4H two CH 2 groups of acetals, 540 (s, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO AnalCalcdFor C 6 H 4 F 5 C: 478, H: 346, N: 032 and F: 2332% Found: C: 4638, H: 296, N: 972 and F: 2252% Cyclohexyl ((4, 5-bis (hydroxymethyl- H-imidazol--yl methyl carbamate (5a Yield 60% m p: C IR (KBr: 3520 (ν O-H, intramolecular H-bonding, 3020 (stretching of Ar-H, (N-H, 2940 and 2895 (CH 2 of aliphatic C-H stretching, 75 (C=O, 68 (C=N, 46 (C-N and 322 cm - (C-O respectively H-NMR (400 MHz, DMSO-d (m, 0H, CH 2 of cyclohexyl, 39 (m, H, O-CH of cyclohexyl, 425 (s, 2H two OH having intramolecular H-bonding, 473 (s, 4H two CH 2 groups of dimethanols, 540 (s, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO AnalCalcdFor C 3 H 2 C: 55, H: 747 and N: 483% Found: C: 543, H: 697 and N: 423% Tetrahydro-2H-piran-4-yl ((4,5-bis (hydroxymethyl- H -imidazol--yl methyl carbamate (5b Yield 65% m p: C IR (KBr: 3520 (ν O-H, intramolecular H-bonding, 3030 (stretching of Ar-H, (N-H, 2940 and 2895 (CH 2 of aliphatic C-H stretching, 75 (C=O, 620 (C=N, 48 (C-N and 324 cm - (C-O respectively H-NMR (400 MHz, DMSO-d (m, 4H CH 2 of pyran, (t, 4H, CH 2 -O of pyran, 420 (s, 2H two OH having intramolecular H-bonding, 407 (m, H, O-CH of pyran, 473 (s, 4H two CH groups of dimethanols, 540 (s, 2H, N-CH, 757 (s, H of imidazole ring and 803 (s, 2 2 H, NH-CO For C 2 H 9 O 5 C: 55, H: 747 and N: 483% Found: C: 543, H: 697 and N: 423% Tetrahydro-2H-thiopiran-4-yl ((4,5-bis (hydroxymethyl- H -imidazol--yl methyl carbamate (5c Yield 62% m p: C IR (KBr: 3520 (ν O-H, intramolecular H-bonding, 3045 (stretching of Ar-H, (N- H, 2940 and 2895 (CH 2 of aliphatic C-H stretching, 75 (C=O, 620 (C=N, 48 (C-N, 324 cm - (C-O and 75 cm - (C-S respectively H-NMR (400 MHz, DMSO-d (m, 4H, CH 2 of thiopyran, (t, 4H, -CH 2 S of thiopyran, 420 (s, 2H two OH having intramolecular H-bonding, 47 (m, H, O-CH of thiopyran, 473 (s, 4H two CH 2 groups of dimethanols, 540 (s, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO For C 2 H 9 S C: 4783, H: 635, N: 394 and S: 064% Found: C: 4703, H: 585, N: 334 and S: 044% Perfluorophenyl ((4, 5-bis(hydroxymethyl- H-imidazol--yl methyl carbamate (5d Yield 75% m p: 69-7 C IR (KBr: 3520 (ν O-H, intramolecular H-bonding, 3035 (stretching of Ar-H, (N-H, 2940 and 2895 (CH 2 of aliphatic C-H stretching, 75 (C=O, 620 (C=N, 420 (C-N, 326 cm - (C-O and 00 cm - (C-F respectively H-NMR (400 MHz, DMSO-d (s, 2H two OH having intramolecular H-bonding, 473 (s, 4H two CH 2 groups of dimethanols, 540 (s, 2H, N-CH 2, 757 (s, H of imidazole ring and 803 (s, H, NH-CO For C 3 H 0 F 5 C: 4252, H: 274, N: 44 and F: 2587% Found: C: 472, H: 224, N: 084 and F: 2507% JOMC Volume 33 Issue June, 206 2

3 Cyclohexyl ((6-oxide-6-(3-phenylureido-4,8-dihydro-H-[,3,2] dioxaphosphepino[5,6-d] imidazole--yl methyl carbamate 7(a The obtained product of 7a is 088 g, Yield 64% m p: 49-5 C IR (KBr: (γ P-NH, 3040 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 675 (C=O of urea, 68 (C=N, 46 (C-N, 320 (γ C-O, 250(γ P=O and 950 cm - (γ P-O respectively H-NMR (400 MHz, DMSO-d 6 : (m, 0H, CH of cyclohexyl, 39 (m, H, O-CH of PPM 2 cyclohexyl, 523 (s,4h, two CH 2, 60 (s, 2H, NH-of urea moiety, (m, 5H H 5 attached to urea moiety,757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 : 373, 329, 277, 634, 606, 68, 562, 768, 308, 24, 257, 520, 375, 208, 290 and 333 corresponding to PPM C and C 3, C and C 20, C 7 and C 9 and C 3 8 P-NMR (689 MHz, DMSO-d 6 : -690, -645 For C H N O P C: 583, H: 565, N: 5 and P: 668% Found: C: 503, H: 55, N: 45 and P: 598% PPM Tetrahydro-2H-pyran-4-yl ((6-oxide-6-(3-phenylureido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate 7(b The obtained product of 7b is 093 g Yield 67% m p: C IR (KBr: (γ P-NH, 3040 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 675 (C=O of urea, 68 (C=N, 46 (C-N, 320 (γ C-O, 250(γ P=O and 950 cm - (γ P-O respectively H-NMR (400 MHz, DMSO-d (m, 4H, CH 2 of pyran, (t, 4H, CH 2 -O of pyran, 407 (m, H, O-CH of pyran, 523 (s, 4H two CH 2, 60 (s, 2H, NH-of urea moiety, (m, 5H H 5 attached to urea moiety,757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 725, 334, 632, 520, 394, 26, 289 and 280 PPM corresponding to C and C, C 3 and C 9 3 P-NMR (689 MHz, DMSO-d 6 : -695, -653 For C H N O P C: 4903, H: 520, N: 505 and P: 666% Found: C: 4823, H: 470, N: 445 PPM and P: 596% Tetrahydro-2H-thiopyran-4-yl ((6-oxide-6-(3-phenylureido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate 7(c The obtained product of 7c is 093 g Yield 65% m p: C IR (KBr: (γ P-NH, 3040 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 675 (C=O of urea, 620 (C=N, 46 (C-N, 320 (γ C-O, 250(γ P=O, 950 (γ P-O and 75 cm - (C-S respectively H-NMR (400 MHz, DMSO-d (m, 4H, CH 2 of thio pyran, (t, 4H, CH 2 -S of thiopyran, 47 (m, H, O-CH of thiopyran, 523 (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, 2H, NH-of urea moiety, (m, 5H H 5 attached to urea moiety,757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 695, 332, 255, 520, 394, 26, 289 and 280 corresponding to C and C, C 3 and C 9 3 P-NMR (689 MHz, DMSO-d 6-704, -642 For C 9 H 24 PS : 4740, H: 502, N: 455, P: 643 and S: 666% Found: C: C 4660, H: 452, N: 395, P: 573 and S: 646% Perfluorophenyl ((6-oxide (3-phenylureido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7d The obtained product of 7d is 095 g Yield 70% m p: C IR (KBr: (γ P-NH, 3040 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 675 (C=O of urea, 622 (C=N, 46 (C-N, 320 (γ C-O, 250(γ P=O, 00 (C-F and 950 cm - (γ P-O respectively H-NMR (400 MHz, DMSO-d (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, 2H, NH-of urea moiety, (m, 5H H 5 attached to urea moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 550, 420, 393, 424, 40, 520, 394, 26, 289 and 280 corresponding to C and C 3, C and C 20, C 7 and C 9 and C 3 8 P-NMR (689 MHz, DMSO-d For C H F N O P C: 4389, H: 276, F: PPM , N: 280 and P: 566% Found: C: 4309, H: 226, F: 656, N: 220 and P: 496% Cyclohexyl ((6-(3-(4-methoxyphenyl ureido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate 7(e The obtained product of 7e is 094 g Yield 64% m p: C IR (KBr: (γ P-NH, 3025 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 670 (C=O of urea, 66 (C=N, 46 (C-N, 320 (γ C-O, 250 (γ P=O and 950 cm - (γ P-O respectively H-NMR (400 MHz, DMSO-d (m, 0H, CH 2 of cyclohexyl, 383 (s, 3H, CH 3 of methoxyphenyl, 39 (m, H, O-CH of cyclohexyl, 523 (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, 2H, NH-of urea moiety, 6,97-75 (m, 4H H 4 attached to urea moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 768, 308, 24, 257, 520, 37, 98, 45, 589 and 568 corresponding to C and C 3, C and C 20, C 7 and C 9, C 8 and C 2 3 P-NMR (689 MHz, DMSO-d 6 : -608, -56 For C H N O P C: 5, H: 572, N: 49 and P: 628% Found: C: 503, H: 552, N: 359 and P: 558% Tetrahydro-2H-pyran-4-yl ((6-(3-(4-chlorophenylureido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole- -yl methyl carbamate 7(f The obtained product of 7f is 0 g Yield 68% m p: C IR (KBr: (γ P-NH, 3027 (Ar-H, 2940 and 2895 Issue June, 206 3

4 (aliphatic C-H stretching, 705 (C=O of ester group, 680 (C=O of urea, 68 (C=N, 46 (C-N, 320 (γ C-O, 950 (γ P-O and 730 cm - (C-Cl respectively H-NMR (400 MHz, DMSO-d (m, 4H, CH 2 of pyran, 365 and 355 (t, 4H, CH 2 -O of pyran, 407 (m, H, O-CH of pyran, 523 (s, 4H two CH 2, 60 (s, 2H, NH-of urea moiety, (m, 4H H 4 attached to urea moiety, 757 (s, H of imidazole ring and 803 (s, H, NH- CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 725, 334, 632, 520, 394, 26, 289 PPM and 280 corresponding to C and C, C 3 and C 9 3 P-NMR (689 MHz, DMSO-d For C 9 H 23 Cl P C: 4566, H: 464, Cl: 709, N: 409 and P: 620% Found: C: 4486, H: 44, Cl: 629, N: 34 and P: 550% Tetrahydro-2H-thiopyran-4-yl ((6-(3-(4-bromophenylureido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate 7(g The obtained product of 7g is 2 g Yield 67% m p: C IR (KBr: (γ P-NH, 3029 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 680 (C=O of urea, 68 (C=N, 46 (C-N, 320 (γ C-O, 250 (γ P=O, 950 (γ P-O and 75 cm - (C-S respectively H-NMR (400 MHz, DMSO-d (m, 4H, CH 2 of thio pyran, 257 and 247 (t, 4H, CH 2 -S of thiopyran, 47 (m, H, O-CH of thiopyran, 523 (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, 2H, NH-of urea moiety, (m, 4H H 4 attached to urea moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 696, 322, 255, 520, 384, 29, 38 and 223 corresponding to C and C, C 3 and C 9 and C 8 and C 3 7 P-NMR (689 MHz, DMSO-d For C H BrN O PS C: 4072, H: 44, Br: 426, N: 250, P: 553 and PPM S: 572% Found: C: 4003, H: 369, Br: 366, N: 60, P: 493 and S: 552% Perfluorophenyl ((6-(3-(4-nitrophenyl ureido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate 7(h The obtained product of 7h is 06 g Yield72% m p: C IR (KBr: (γ P-NH, 3030 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 705 (C=O of ester group, 685 (C=O of urea, 622 (C=N, 46 (C-N, 320 (γ C-O, 250 (γ P=O, 950 (γ P-O and 00 cm - (C-F respectively H-NMR (400 MHz, DMSO-d 6 : δ : 523 (s, 4H two CH groups attached to PPM 2 phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, 2H, NH-of urea moiety, (m, 4H H 4 attached to urea moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 550, 420, 393, 424, 40, 520, 455, 99, 24 and 435 corresponding to C and C 3, C 0, C and C 20, C 7 and C 9 and C 3 8 P-NMR (689 MHz, DMSO-d 6 : -785, -750 For C H F N O P C: PPM , H: 238, F: 604, N: 49 and P: 523% Found: C: 3975, H: 88, F: 584, N: 359 and P: 453% Cyclohexyl ((6-(morpholine-4-carboxamido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7i The obtained product of 7i is 09 g Yield : 67% M p: C IR (KBr: (γ P-NH, 3030 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 66 (C=N, 46 (C-N, 320 (γ C-O and 950 cm - (γ P-O respectively δ : (m, 0H, CH of cyclohexyl, 33 (t, 4H, N-CH of morpholine ring J=7Hz, 365 (t, 4H, -CH 2 -O of morpholine ring J=7Hz, 430 (m, H, CH of cyclohexyl ring attached to oxygen, 523 (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 C-NMR(75 MHz, DMSO-d 6 373, 329, 277, 634, 606, 68, 562, 768, 308, 24, 257, 585, 394, 463 and 657 corresponding to C and C 3, C and C 6 3 P-NMR (689 MHz, DMSO-d 6 PPM : -695 Anal Calcd(% For C 8 H 28 P C: 4726, H: 67, N: 53 and P: 677% Found: C: 4666, H: 567, N: 47 and P: 677% Tetrahydro-2H-pyran-4-yl ((6-(morpholine-4-carboxamido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole- -yl methyl carbamate (7j The obtained product of 7j is 096 g, Yield : 70%m p: C IR (KBr: (γ P-NH, 3034 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68(C=N, 46 (C-N, 320 (γ C-O and 950 cm - (γ P-O respectively δ : (m, 4H, CH pyran of carbamate, 33 (t, 4H, N-CH of morpholine ring, 365 (t, 4H, -CH 2 -O of morpholine ring J=7Hz, 385 (t, 4H, CH 2 -O pyran of carbamate J=7Hz, 47 (m, H, O-CH pyran of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 725, 334, 632, 585, 463 and 657 corresponding to C and C, C 3 and C 5 and C 6 AnalCalcd (% For C 7 H 26 O 8 P C: 4445, H: 570, N: 524 and P: 674% Found: C: 4365, H: 520, N: 464 and P: 604% JOMC Volume 33 Issue June, 206 4

5 Tetrahydro-2H-thiopyran-4-yl ((6-(morpholine-4-carboxamido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7k The obtained product of 7k is 098 g, Yield: 69%m p: C IR (KBr: (γ P-NH, 300 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68(C=N, 46 (C-N, 320 (γ C-O, 950 (γ P-O and 75 cm - (C-S respectively δ : (m, 4H, CH thio pyran of carbamate, 257 (t, 4H, CH -S thiopyran of carbamate, 33 (t, 4H, N-CH 2 of morpholine ring J=7Hz, 365(t, 4H, -CH 2 -O of morpholine ring J=7Hz, 40 (m, H, O-CH thiopyran of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 695, 322, 255, 585, 463 and 657 corresponding to C and C, C 3 and C 5 and C 6 AnalCalcd (% For C 7 H 26 PS C: 4294, H: 55, N: 473, P: 65 and S: 674% Found: C: 424, H: 50, N: 43, P: 58 and S: 654% Perfluorophenyl ((6-(morpholine-4-carboxamido-6-oxide-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7l The obtained product of 7l is 0 g, Yield: 75%m p: 69-7 C IR (KBr: (γ P-NH, 3020 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68(C=N, 46 (C-N, 320 (γ C-O, 00 (C-F and 950 cm - (γ P-O respectively δ : 33 (t, 4H, N-CH of morpholine ring J=7Hz, 365 (t, 4H, -CH -O of morpholine ring J=7Hz, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 550, 420, 393, 424, 40, 463, 657 and 463 corresponding to C and C 3, C and C 6 AnalCalcd (% For C 8 H 7 F 5 P C: 3994, H: 37, F: 755, N: 294 and P: 572% Found: C: 394, H: 267, F: 675, N: 234 and P: 502% Cyclohexyl ((6-oxido-6-(piperidine--carboxamido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7m The obtained product of 7m is 088 g, Yield: 65% m p: C IR (KBr: (γ P-NH, 3025 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68(C=N, 46 (C-N, 320 (γ C-O and 950 cm - (γ P-O respectively δ : (m, 0H, CH cyclohexyl of carbamate, (m, 6H, CH piperidine of carboxamide, 377 (t, 4H, N-CH 2 piperidine of carboxamide J=7Hz, 39 (m, H, O-CH cyclohexyl of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 768, 308, 24, 257, 565, 490, 249 and 238 corresponding to C and C 3, C and C 9 3 P-NMR (689 MHz, DMSO-d 6 PPM : -505 AnalCalcd (% For C 9 H 30 P C: 50, H: 664, N: 538 and P: 680% Found: C: 493, H: 64, N: 478 and P: 60% Tetrahydro-2H-pyran-4-yl ((6-oxido-6-(piperidine--carboxamido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole- -yl methyl carbamate (7n The obtained product of 7n is 096 g, Yield: 70% m p: C IR (KBr: (γ P-NH, 3027 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68(C=N, 46 (C-N,320 (γ C-O and 950 cm - (γ P-O respectively δ : (m, 6H, CH piperidine of carboxamide, (m, 4H, CH pyran of carbamate, 377 (t, 4H, N-CH 2 piperidine of carboxamide J=7Hz, (m, 4H, CH 2 -O pyran of carbamate, 407 (m, H, O-CH pyran of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 725, 334, 632, 565, 490, 249 and 238 corresponding to C and C, C 3 and C 6 AnalCalcd (% For C 8 H 28 P C: 4726, H: 67, N: 53 and P: 677% Found: C: 4646, H: 567, N: 47 and P: 607% Tetrahydro-2H-thiopyran-4-yl ((6-oxido-6-(piperidine--carboxamido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7o The obtained product of 7o is 089 g, Yield: 63%m p: C IR (KBr: (γ P-NH, 3029 (Ar-H, 2940 and JOMC Volume 33 Issue June, 206 5

6 2895 (aliphatic C-H stretching, 650 (C=O, 620 (C=N, 46 (C-N, 320 (γ C-O, 950 (γ P-O and 75 cm - (C-S respectively δ : (m, 6H, CH piperidine of carboxamide, (m, 4H, CH thio pyran of carbamate, 257 (t, 4H, CH 2 -S thio pyran of carbamate J=7Hz, 377 (t, 4H, N-CH 2 piperidine of carboxamide J=7Hz, 47 (m, H, O-CH thio pyran of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 695, 322, 255, 565, 490, 249 and 238 corresponding to C and C 2 and C, C 3 and C 6 AnalCalcd (% For C 8 H 28 PS C: 4566, H: 596, N: 479, P: 654 and S: 677% Found: C: 4486, H: 546, N: 49, P: 584 and S: 657% Perfluorophenyl ((6-oxido-6-(piperidine--carboxamido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7p The obtained product of 7p is 0 g, Yield: 75% m p: C IR (KBr: (γ P-NH, 3030 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 622 (C=N, 46 (C-N, 320 (γ C-O, 00 (C-F and 950 cm - (γ P-O respectively δ : (m, 6H, CH piperidine of carboxamide, 377 (t, 4H, N-CH piperidine of carboxamide J=7Hz, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 550, 420, 393, 424, 40, 565, 490, 249 and 238 corresponding to C and C 3, C and C 9 AnalCalcd (% For C 9 H 9 F 5 P C: 425, H: 355, F: 76, N: 298 and P: 574% Found: C: 43, H: 305, F: 68, N: 238 and P: 504% Cyclohexyl ((6-(4-methylpiperazine--carboxamido-6-oxido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7q The obtained product of 7q is 09 g, Yield: 65% m p: C IR (KBr: (γ P-NH, 3025 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 66 (C=N, 46 (C-N,320 (γ C-O and 950 cm - (γ P-O respectively δ PPM : (m, 0H, CH 2 cyclohexyl of carbamate, 226 (s, 3H, N-CH 3, 227 (t, 4H, CH 2 -N piperazine of carboxamide J=7Hz, 340 (t, 4H, N-CH 2 piperazine of carboxamide J=7Hz, 39 (m, H, O-CH of cyclohexyl of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 768, 308, 24, 257, 585, 54, 50 and 466 corresponding to C and C 3, C and C 9 3 P-NMR (689 MHz, DMSO-d 6 PPM : -70 AnalCalcd (% For C 9 H 3 N 6 P C: 485, H: 664, N: 786 and P: 658% Found: C: 477, H: 64, N: 726 and P: 588% Tetrahydro-2H-pyran-4-yl ((6-(4-methylpiperazine--carboxamido-6-oxido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (7r The obtained product of 7r is 09 g, Yield: 70% m p: C IR (KBr: (γ P-NH, 3027 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 68 (C=N, 46 (C-N, 320 (γ C-O and 950 cm - (γ P-O respectively δ PPM : 72-97(m, 4H, CH 2 pyran of carbamate, 226 (s, 3H, N-CH 3, 227 (t, 4H, CH 2 -N piperazine of carboxamide J=7Hz, 340 (t, 4H, N-CH 2 piperazine of carboxamide J=7Hz, 385 (t, 4H, CH 2 -O pyran of carbamate J=75Hz, 407 (m, H, O-CH pyran of carbamate, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 562, 725, 334, 632, 585, 54, 50 and 466 corresponding to C and C, C 3 and C 6 AnalCalcd (% For C 8 H 29 N 6 P C: 4576, H: 69, N: 779 and P: 656% Found: C: 4496, H: 569, N: 79 and P: 586% Tetrahydro-2H-thiopyran-4-yl ((6-(4-methylpiperazine--carboxamido-6-oxido-4,8-dihydro- H-[,3,2]dioxaphosphepino[5,6-d] imidazole--yl methyl carbamate (7s The obtained product of 7s is 098 g, Yield: 67% m p: C IR (KBr: (γ P-NH, 3029 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 620 (C=N, 46 (C-N, 320 (γ C-O, 950 (γ P-O and 75 cm - (C-S respectively Issue June, 206 6

7 δ : (m, 4H, CH thio pyran of carbamate, 226 (s, 3H, N-CH, 227 (t, 4H, PPM 2 3 CH 2 -N piperazine of carboxamide J=7Hz, 257 (t, 4H, CH 2 -S thiopyran of carbamate J=7Hz, 340 (t, 4H, N-CH 2 piperazine of carboxamide J=75Hz, 47 (m, H, O-CH thiopyran of carbamate, 523 (s, 4H two CH 2 groups attached to phosphorus moiety, 540 (s, 2H, N-CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 : 373, 329, 277, 634, 606, 68, 562, 695, 332, 255, 585, 54, 50 and 466 corresponding to C and C, C 3 and C 6 AnalCalcd (% For C 8 H 29 N 6 PS C: 4426, H: 598, N: 720, P: 634 and S: 656% Found: C: 4346, H: 548, N: 660, P: 564 and S: 636% Perfluorophenyl ((6-(4-methylpiperazine--carboxamido-6-oxido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazole- -yl methyl carbamate (7t The obtained product of 7t is 00 g, Yield: 73% m p: CIR (KBr: (γ P-NH, 3030 (Ar-H, 2940 and 2895 (aliphatic C-H stretching, 650 (C=O, 622 (C=N, 46 (C-N, 320 (γ C-O, 00 (C-F and 950 cm - (γ P-O respectively δ : 226 (s, 3H, N-CH, 227 (t, 4H, CH -N piperazine of carboxamide J=7Hz, 340 (t, 4H, PPM 3 2 N-CH 2 piperazine of carboxamide J=7Hz, 523 (s, 4H two CH 2, 60 (s, H, NH-of carboxamide moiety, 757 (s, H of imidazole ring and 803 (s, H, NH-CO 3 373, 329, 277, 634, 606, 68, 550, 420, 393, 424, 40, 585, 54, 50 and 466 corresponding to C and C 3, C, C 5 and C 9 AnalCalcd (% For C 9 H 20 F 5 N 6 P C: 46, H: 364, F: 74, N: 56 and P: 559% Found: C: 4036, H: 34, F: 634, N: 456 and P: 489% RESULTS AND DISCUSSION Synthesis of 2-(6,6-dimethyl-4,8-dihydro- H-[,3] dioxepino[5,6-d] imidazole--yl acetyl azide (2 [5] To a solution of 2-(6,6-dimethyl-4,8-dihydro-H-[,3] dioxepino [5,6-d] imidazol--yl-acetic acid (45 g, 002 mol ( in acetone was added triethyl amine (050 ml and stirred for 30 minutes To the reaction mixture aqueous Na (06 mol was added and stirred for 20 minutes at 0 C After completion, reaction mixture was poured in ice cold water (20 ml, extracted with diethyl ether (0 ml The organic layer was separated, washed with water, brine, dried over anhydrous Na 2 S, filtered and evaporated under vacuum to give crude product The crude product was purified by column chromatography (60-20 mesh silica gel, eluent: 0 % EtoAc-pet ether, to give pure acid azide (35 g (2 This was collected by filtration and recrystallized from ethanol, mp C, yield 70% Synthesis of Cylohexyl/tetrahydro-2H-pyran/tetrahydro-2H-thiopyran/perfluoro phenyl (6,6-dimethyl-4,8-dihydro- H-[,3] dioxepino [5,6-d] imidazol--yl methyl carbamates 4(a-d [6] To the solution if acid azide (2 (09 g mol, in Cyclohexanol (5 ml, 0 mol (3a was added and reaction mixture was refluxed for 6 hours After completion of the reaction, solvent was evaporated under vacuum to give crude residue, which was purified by column chromatography (60-20 mesh silica gel The reaction was monitored with TLC using hexane and ethylacetate (7:3 as an eluent Ethylacetate and petroleum ether (3:7 solvent mixture was used as an eluent Finally the product compound cyclohexyl ((6,6-dimethyl-4,8-dihydro-H-[,3] doxepin [5,6-d] imidazol--yl methyl carbamate (087 g (4a was purified from aqueous dimethyl formamide Yield 68%, m p C The similar experimental procedure was adopted to synthesize 4(b-d (4b-088 g with 68%, 4c-087 g with 68%, 4d-079 g with 70% from 2 and Tetrahydro-2H-pyron-4-ol (3b-5 ml, 0074 mol, Tetrahydro-2H-pyron-4-ol (3c-5 ml, 0047 mol and 2, 3, 4, 5, 6-pentafluorophenol (3d-5 ml, 008 mol Synthesis of Cyclohexyl/tetrahydro-2H-pyran-4-yl/tetrahydro-2H-thiopyran-4-yl/pefluorophenyl ((4, 5-bis (hydroxymethyl- H- imidazol--yl methyl carbamates 5(a-d The isopropylidenation of, 2-diols was carried out by a procedure as reported in the literature A suspension of the cyclohexyl ((6,6-dimethyl-4,8-dihydro-H-[,3] doxepin [5,6-d] imidazol--yl methyl carbamate (085 g, mol (4a ( m mol in dry acetone and to this 5 mol% of phosphotungstic acid was added and the reaction mixture was stirred at room temperature under nitrogen atmosphere for hour The progress of the reaction was monitored by TLC using cyclohexane and ethyl acetate (7:3 solvent mixture as an eluent After completion of the reaction, the solvent was removed under reduced pressure The residue was extracted with dichloromethane (3 20 ml and water and the combined organic layer was dried with Na 2 S and concentrated in vacuum to give the crude product (5a The crude product was purified by column chromatography on silica gel (60-20 mesh with 5-30% ethyl acetate in cyclohexane as an eluent The m p of (08 g (5a was C with yield of 60% The similar procedure was adopted to synthesize 5(b-d (5b-084 g with 65%, 5c-086 g with 62%, and 5d-077 gr with 75% from (4b-085 g, mol, 4c-085 g, mol and 4d-077 g, 0007 mol Issue June, 206 7

8 Synthesis of Cyclohexyl/terahydro-2H-pyran/tetrahydro-2H-thiopyran/perfluorophenyl ((6-oxide-6-(3-phenylureido/(4-methoxyphenyl/(4-chlorophenyl/(4-bromophenyl/(4-nitrophenyl ureido-4,8-dihydro- H-[,3,2] dioxaphosphepino [5,6-d] imidazol--yl methyl carbamates 7(a-h A solution of (phenyl carbamoyl phosphoramidic dichloride (50 g, 009 mol [7] (6a (2 mmol in 25 ml of dry toluene was added drop wise over a period of 20 minutes to a stirred solution of Cyclohexyl ((4, 5-bis (hydroxymethyl-h-imidazol-- yl methyl carbamate (080 g, 0003 mol (5a and triethylamine in 30 ml of dry toluene and 0 ml of tetrahydrofuran at 5 C After completion of the addition, the temperature of the reaction mixture was slowly raised to room temperature and stirred for 2 hours Later on the reaction mixture was heated to C and maintained for 4 hours with stirring The completion of the reaction was monitored by TLC analysis Triethyl amine hydrochloric acid was filtered from mixture and solvent was removed under reduced pressure The residue was washed with water and then recrystallized from aqueous 2-propanol to get pure compound cyclohexyl ((6-oxide-6-(3-phenylureido-4,8-dihydro-H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (080 g, 0009 mol (7a, yield 64%, m p 49-5 C The similar procedure was adopted to synthesize 7(b-d (083 g-7b; 083 g-7c; 076 g-7d by the reaction between 5(b-d (083 g, 0003 mol-5b; 085 g, 0003 mol-5c; 075 g, mol-5d with (phenyl carbamoyl phosphoramidic dichloride (50 g, 009 mol (6a, 7(e-h (084 g-7e; 09 g-7f; 099 g-7g; 096 g-7h were prepared by condensation of 5a (084 g, 0003 mol + 6b (50 g, 007 mol, 5b (085 g, 0003 mol + 6c (50 g, 007 mol, 5c (090 g, 0003 mol + 6d (50 g, 005 mol and 5d (09 g, mol + 6e (50 g, 006 mol respectively Synthesis of Cyclohexyl/tetrahydro-2H-pyran-4-yl/tetrahydro-2H-thiopyran-4-yl/perfluorophenyl ((6-(morpholine-4-carboxamido/(piperidine--carboxamido/(4-methylpiperazine--carboxamido-6-oxide-4,8-dihydro- H -[,3,2] dioxaphosphepino [5,6-d]imidazole--yl methyl carbamates 7(i-t A solution of morpholino carbamoyl phosphoramidic dichloride [8] (6a (5 ml, 0060 mole in 25 ml of dry toluene was added drop wise over a period of 20 minutes to a stirred solution of Cyclohexyl ((4, 5-bis (hydroxymethyl-h-imidazol--yl methyl carbamate (084 g, 0003 mol (5a and triethylamine (6 ml, 0004 mole in 30 ml of dry toluene and 0 ml of tetrahydrofuran at 5 C After completion of the addition, the temperature of the reaction mixture was slowly raised to room temperature and stirred for 2 hours Later the reaction mixture was heated to C and maintained for 4 hours with stirring The completion of the reaction was monitored by TLC analysis Triethyl amine hydrochloric acid was filtered from mixture and solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (60-20 mesh with 30% of ethylacetate in cyclohexane as anelutent to afford Cyclohexyl ((6-(morpholine-4-carboxamido-6-oxide-4,8-dihydro-H-[,3,2] dioxaphosphepino [5,6-d] imidazole--yl methyl carbamate (09 g of (7i with yield 67%, m p C The similar procedure was adopted to synthesize 7(j-t by the reaction between 5(b-d (5b-085 g, 0003 mol; 5c-090 g, 0003 mol; 5d-09 g, mol with morpholino carbamoyl phosphoramidic dichloride (5 ml, 006 mol (6a, 7(j-t (7j-096 g, 7k-098 g, 7l-0 g, 7m-088 g, 7n-096 g, 7o-089 g, 7p-0 g, 7q-09 g, 7r-099 g, 7s-098 g, 7t-0 g were prepared by condensation of 5(a-d with (piperidene--carbonyl phosphoramidic dichloride (5 ml, 006 mol (6b and 4-methylpiperazine- -carbamoyl phosphoramidic dichloride (5 ml, 0056 mol (6c MICROBIOLOGY The determine both the antibacterial and antifungal activity, these newly synthesized compounds was performed according to disc diffusion method, as recommended by the National Committee for Clinical Laboratory The synthesized compounds were used at the concentration of 250μg/ml DMF as a solvent [8] Antibacterial assay The antibacterial activity of Carbamates containing imidazole ureas/caboxamides dioxaphosphepinoes 7(a-t were screened against the Staphylococcus aureus NCCS 2079 and Bacillus cerus NCCS 206 (gram positive and Escherichia coli NCCS 2065 Antifungal activity of Carbamates containing imidazole ureas/carboxamides dioxaphosphepinoes 7(a-t were screened against Aspergillus niger NCCS 96 and Candida albicans NCCS 347 Here Ketoconazole is tested as reference compound to compare the activity and Pseudomonasaeruginosa NCCS 2200 (gram negative organisms Here Amoxicillin is tested as reference compound to compare the activity Antifungal assay Most of the compounds exhibit good antibacterial and antifungal activity against both given microorganism The presence of nitro, chloro and bromo were showed more activity than other substituted compounds The Anti-bactterial and anti-fungal activity of 7(a-t was shown in Table Table Anti-bacterial and anti-fungal activity of Carbamates containing imidazole ureas/carboxamides dioxaphosphepinoe 7(a-t SNO COMP R X Zone of inhibition(mm 250 (µg/disc Anti-bacterial activity a Anti-fungal activity b Sa Bc Ec Pa An Ca Issue June, 206 8

9 7a H b H c H d H e OCH f * Cl g * Br h * NO i j k - O l m - CH n - CH o - CH p - CH q - * NCH r - * NCH s - * NCH t - * NCH Amoxicillin Ketoconazole a Abbreviations: Sa: Staphylococcus aureus, Bc: Bacillus cereus, Ec: Escherichia coli, Pa: Pseudomonas aeruginosa b An: Aspergillus niger, Ca: Candida albicans * Indicates more activity CONCLUSION In conclusion, we have demonstrated the synthesis of Organo Phospho Carbamates containing imidazole ureas/carboxamides of 7(a-t involving the four more synthetic steps was required In case of Organo phosphoimidazole derivatives which are proved to be having great potential for the different pharmacological activities (Scheme Scheme- Synthesis of organo phospho carbamates containing imidazole ureas/carboxamides Issue June, 206 9

10 ACKNOWLEDGEMENT The author VEsther Rani thanks to U G C-S A P and U G C-B S R, New Delhi for financial assistance They are also thankful to IICT Hyderabad and CDRI Lucknow for spectral and analytical data REFERENCES Lunt E (987 Antitumor imidazotetrazines 4 Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,-d]-,2,3,5-tetrazinones and 8-substituted pyrazolo[5,-d]-,2,3,5-tetrazinones J Med Chem 30: Robertson DW (985 Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinylphenyl]-H-imidazo[4,5-c]pyridine J Med Chem 28: Suzuki M (986 Boll chem farm 34: Johnson RA (999 Inhibitory effect of 4-(4-fluorophenyl-2-(4-hydroxyphenyl-5-(4-pyridylH-imidazole on HCMV DNA replication and permissive infection Anti viral research 4: 0-5 Brewer MD (987 Isothiourea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,-b]thiazole with broad-spectrum anthelmintic activity J Med Chem 30: Nathanson JA (985 Phenyliminoimidazolidines Characterization of a class of potent agonists of octopamine-sensitive adenylate cyclase and their use in understanding the pharmacology of octopamine receptors Mol Pharmacol 28: Breuer E (996 The Chemistry of Organophosphorus Compounds, John Wiely and Sons Ltd, Newyork 4: Faraci WS (995 Inhibition of Helicobacter pylori Urease by Phenyl Phosphorodiamidates: Mechanism of Action Bioorg Med Chem 3: Fest C, Schmidt KJ (982 The chemistry of organophosphorus pesticides Springer-Verlag, Berlin 2 0 Nivarkar (2004 Tetrahedron Lett 45: 6863 Haranadha Reddy Y (202 Synthesis and Bioassay of α-aminophosphonates Der chemica Sinica 3: Mehellou Y (2007 J Bioorg Med chem Lett 7: Bouchareb F (202 Efficient Method for the Synthesis of Diazaphospholidines: Toxicological Evaluation American journal of organic chemistry 2: Kirsanov AV, Levchenko ES (957 Chem Abstr 5: (200 Indian journal of chemistry 47B: Helene L, Leogane O (2005 Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement Organic Letters 7: Vanladinpuia K, Bez G (20 Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage Tetrahedron Letters 52: Bharadwaj S (20 Scholar Research Library, Achieves of Applied Science Research 3: JOMC Volume 33 Issue June,