SUPPORTING INFORMATION. Studies on antimicrobial evaluation of some 1-((1-(1H-benzo[d]imidazol-2-
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1 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*, iraj Shihory, Malay Bhatt, Bonny Patel and Tushar Karkar (DST-FIST Sponsored & UGC O-SAP), Division of Medicinal Chemistry Department of Chemistry, Mahatma Gandhi Campus Maharaja Krishnakumarsinhji Bhavnagar University Bhavnagar , India dnisheeth@rediffmail.com Contents: Sr o. Description Page o. 1 Experimental of 4b to 4o Antibacterial assay Antifungal assay 9 4 IR, 1 H MR and Mass Spectral files of compound 4a-o
2 1. EXPERIMETAL oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4b) Dark brown amorphous (EtOH). Yield: 75%; m.p C; IR (KBr, cm -1 ): 3444 (OH), 3332 (-H, benzimidazole), 3052 (C-H, aromatic), 2923 (C-H, CH 3 ), 2212 (C), 1685 (CO), 1642 (C=C), 1562 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ), (m, 13H, Ar-H), 5.70 (s, 1H, OH), 9.27 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.6, 163.7, 161.2, 160.2, 155.6, 153.1, 151.5, 134.8, 133.0, 132.5, 132.1, 128.9, 128.6, 127.9, 123.4, 121.4, 118.5, 117.8, 115.9, 115.5, 115.0, 114.8, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 19 7 O 2 ): C, 70.01; H, 3.85;, 19.71%. Found: C, 69.78; H, 3.42;, 19.56%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((2-hydroxybenzylidene)amino)-2-1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((3-hydroxybenzylidene)amino)-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4c) Light brown amorphous (EtOH). Yield: 73%; m.p C; IR (KBr, cm -1 ): 3440 (OH), 3333 (-H, benzimidazole), 3051 (C-H, aromatic), 2924 (C-H, CH 3 ), 2213 (C), 1683 (CO), 1644 (C=C), 1563 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), (m, 13H, Ar-H), 5.74 (s, 1H, OH), 9.24 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.5, 163.7, 160.1, 158.6, 155.5, 153.2, 151.5, 134.9, 135.0, 132.5, 130.2, 128.9, 128.6, 127.9, 123.0, 121.8, 118.3, 115.8, 115.2, 115.0, 114.8, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 19 7 O 2 ): C, 70.01; H, 3.85;, 19.71%. Found: C, 69.23; H, 3.22;, 19.06%. 2
3 oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4d) Brown amorphous (EtOH). Yield: 79%; m.p C; IR (KBr, cm -1 ): 3444 (OH), 3335 (- H, benzimidazole), 3053 (C-H, aromatic), 2925 (C-H, CH 3 ), 2215 (C), 1684 (CO), 1642 (C=C), 1562 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), (m, 13H, Ar-H), 5.57 (s, 1H, OH), 9.25 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.5, 163.7, 160.8, 160.0, 155.6, 153.2, 151.5, 134.9, 132.4, 130.6, 128.9, 128.6, 127.8, 123.0, 116.0, 115.8, 115.3, 115.2, 114.8, 13.6; LCMS (ESI): m/z: [M + ]. Anal. Calcd For (C 29 H 19 7 O 2 ): C, 70.01; H, 3.85;, 19.71%. Found: C, 69.55; H, 3.52;, 19.46%. phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4e) Reddish brown crystal (EtOH). Yield: 74%; m.p C; IR (KBr, cm -1 ): 3336 (-H, benzimidazole), 3052 (C-H, aromatic), 2928 (C-H, CH 3 ), 2218 (C), 1685 (CO), 1640 (C=C), 1561 (C=), 1528, 1326 (=O, Ar-O 2 ); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.27 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 160.0, 155.6, 153.2, 151.5, 147.8, 134.9, 132.5, 131.9, 130.2, 128.9, 128.6, 128.4, 127.8, 124.0, 123.0, 115.8, 115.3, 115.2, 114.8, 13.6; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 18 8 O 3 ): C, 66.16; H, 3.45;, 21.28%. Found: C, 63.25; H, 3.20;, 20.46%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-hydroxybenzylidene)amino)-2-1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((2-nitrobenzylidene)amino)-2-oxo-4-1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((3-nitrobenzylidene)amino)-2-oxo-4- phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4f) 3
4 Reddish brown crystal (EtOH). Yield: 69%; m.p C; IR (KBr, cm -1 ): 3335 (-H, benzimidazole), 3050 (C-H, aromatic), 2930 (C-H, CH 3 ), 2223 (C), 1684 (CO), 1640 (C=C), 1563 (C=), 1524, 1325 (=O, Ar-O 2 ); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.32 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.26 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.6, 163.8, 160.1, 155.7, 153.2, 151.6, 148.2, 135.3, 134.9, 134.6, 132.6, 131.9, 129.6, 128.9, 128.6, 128.4, 127.8, 124.0, 123.0, 115.8, 115.3, 115.2, 114.8, 13.6; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 18 8 O 3 ): C, 66.16; H, 3.45;, 21.28%. Found: C, 65.25; H, 3.32;, 20.30%. phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4g) Reddish brown crystal (EtOH). Yield: 72%; m.p C; IR (KBr, cm -1 ): 3338 (-H, benzimidazole), 3053 (C-H, aromatic), 2935 (C-H, CH 3 ), 2228 (C), 1684 (CO), 1640 (C=C), 1561 (C=), 1526, 1329 (=O, Ar-O 2 ); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.28 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 160.0, 155.5, 153.2, 151.7, 150.2, 139.8, 134.9, 132.6, 131.9, 128.9, 128.6, 128.4, 127.9, 127.8, 124.0, 123.1, 115.8, 115.3, 115.2, 114.8, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 18 8 O 3 ): C, 66.16; H, 3.45;, 21.28%. Found: C, 66.02; H, 3.20;, 21.01%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-nitrobenzylidene)amino)-2-oxo-4-1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((2-chlorobenzylidene)amino)-2-oxo- 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4h) Pale yellow amorphous (EtOH). Yield: 72%; m.p C; IR (KBr, cm -1 ): 3336 (-H, benzimidazole), 3052 (C-H, aromatic), 2936 (C-H, CH 3 ), 2229 (C), 1686 (CO), 1642 (C=C), 4
5 1562 (C=), 756 (C-Cl); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.29 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.5, 163.7, 160.1, 155.6, 153.2, 151.6, 134.9, 133.9, 133.4, 132.6, 132.4, 131.9, 128.9, 128.6, 128.4, 127.9, 127.2, 126.2, 123.1, 115.8, 115.4, 115.2, 114.7, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 18 Cl 7 O): C, 67.51; H, 3.52;, 19.00%. Found: C, 66.25; H, 3.34;, 18.24%. 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4i) Lemon yellow (EtOH). Yield: 73%; m.p C; IR (KBr, cm -1 ): 3335 (-H, benzimidazole), 3054 (C-H, aromatic), 2938 (C-H, CH 3 ), 2231 (C), 1687 (CO), 1641 (C=C), 1560 (C=), 759 (C-Cl); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.28 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 160.0, 155.6, 153.2, 151.5, 135.1, 134.9, 134.4, 132.6, 131.1, 130.2, 128.9, 128.6, 128.4, 127.9, 127.3, 123.1, 115.8, 115.4, 115.2, 114.7, 13.7; LCMS (ESI) M/Z: [M + ]. Anal. Calcd For C 29 H 18 Cl 7 O: C, 67.51; H, 3.52;, 19.00%. Found: C, 66.00; H, 3.21;, 18.10%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((3-chlorobenzylidene)amino)-2-oxo- 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-chlorobenzylidene)amino)-2-oxo- 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4j) Dark yellow crystal (EtOH). Yield: 68%; m.p C; IR (KBr, cm -1 ): 3338 (-H, benzimidazole), 3052 (C-H, aromatic), 2936 (C-H, CH 3 ), 2234 (C), 1687 (CO), 1641 (C=C), 1561 (C=), 761 (C-Cl); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ),
6 (m, 13H, Ar-H), 9.26 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 160.0, 155.6, 153.2, 151.5, 136.6, 134.9, 132.5, 131.8, 130.6, 128.9, 128.6, 127.9, 123.1, 115.8, 115.4, 115.2, 114.7, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 29 H 18 Cl 7 O): C, 67.51; H, 3.52;, 19.00%. Found: C, 67.10; H, 3.34;, 18.75%. 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4k) 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((2-methylbenzylidene)amino)-2-oxo- Light yellow crystal (EtOH). Yield: 70%; m.p C; IR (KBr, cm -1 ): 3335 (-H, benzimidazole), 3054 (C-H, aromatic), 2931 (C-H, CH 3 ), 2230 (C), 1682 (CO), 1638 (C=C), 1569 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.32 (s, 3H, CH 3 ), 2.50 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.24 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.6, 160.0, 155.6, 153.2, 151.5, 135.6, 134.9, 132.5, 131.1, 130.9, 129.0, 128.9, 128.6, 127.9, 126.5, 125.5, 123.1, 115.8, 115.4, 115.2, 114.7, 18.9, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 30 H 21 7 O): C, 72.71; H, 4.27;, 19.79%. Found: C, 71.12; H, 4.02;, 18.86%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((3-methylbenzylidene)amino)-2-oxo- 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4l) Yellow amorphous (EtOH). Yield: 70%; m.p C; IR (KBr, cm -1 ): 3334 (-H, benzimidazole), 3052 (C-H, aromatic), 2927 (C-H, CH 3 ), 2231 (C), 1682 (CO), 1638 (C=C), 1562 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.31 (s, 3H, CH 3 ), 2.52 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.26 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 160.0, 155.6, 153.2, 151.5, 138.5, 134.9, 133.6, 6
7 132.5, 131.3, 130.9, 129.4, 128.9, 128.7, 128.6, 127.9, 126.2, 123.0, 115.8, 115.4, 115.2, 114.7, 21.3, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 30 H 21 7 O): C, 72.71; H, 4.27;, 19.79%. Found: C, 70.23; H, 3.86;, 18.54%. 4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4m) Light Yellowish amorphous (EtOH). Yield: 78%, m.p C; IR (KBr, cm -1 ): 3337 (-H, benzimidazole), 3050 (C-H, aromatic), 2929 (C-H, CH 3 ), 2230 (C), 1684 (CO), 1637 (C=C), 1562 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), 2.52 (s, 3H, CH 3 ), (m, 13H, Ar-H), 9.24 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.5, 163.6, 160.0, 155.5, 153.2, 151.5, 140.7, 134.9, 132.5, 130.7, 129.1, 128.9, 128.6, 127.9, 123.0, 115.8, 115.4, 115.2, 114.8, 21.3, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 30 H 21 7 O): C, 72.71; H, 4.27;, 19.79%. Found: C, 71.85; H, 4.01;, 19.57%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-methylbenzylidene)amino)-2-oxo- 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-methoxybenzylidene)amino)-2- oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile (4n) Light cream amorphous (EtOH). Yield: 68%; m.p C; IR (KBr, cm -1 ): 3334 (-H, benzimidazole), 3058 (C-H, aromatic), 2929 (C-H, CH 3 ), 2852 (C-H, OCH 3 ), 2223 (C), 1679 (CO), 1632 (C=C), 1564 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), 3.83 (s, 3H, OCH 3 ), (m, 13H, Ar-H), 9.26 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.4, 163.7, 162.9, 160.0, 155.6, 153.2, 151.5, 134.9, 132.5, 130.2, 128.9, 128.6, 127.9, 126.0, 123.0, 115.8, 115.4, 115.2, 114.8, 7
8 114.4, 55.9, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 30 H 21 7 O 2 ): C, 70.44; H, 4.14;, 19.17%. Found: C, 69.55; H, 4.05;, 18.41%. 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-2-oxo-4-phenyl-6-((3,4,5-trimethoxy- benzylidene)amino)-1,2-dihydropyridine-3,5-dicarbonitrile (4o) Light orange crystal (EtOH). Yield: 70%; m.p C; IR (KBr, cm -1 ): 3336 (-H, benzimidazole), 3055 (C-H, aromatic), 2927 (C-H, CH 3 ), 2857 (C-H, OCH 3 ), 2226 (C), 1679 (CO), 1631 (C=C), 1568 (C=); 1 H MR (400 MHz, DMSO-d 6, ppm): δ=1.33 (s, 3H, CH 3 ), (s, 9H, OCH 3 ), (m, 11H, Ar-H), 9.24 (s, 1H, CH=), (s, 1H, -H benzimidazole); 13 C MR (100 MHz, DMSO-d 6, ppm): δ=169.6, 163.6, 160.0, 155.6, 153.2, 151.5, 141.5, 134.9, 132.5, 128.9, 128.6, 128.0, 127.9, 123.0, 115.8, 115.4, 115.2, 114.8, 104.2, 60.9, 56.1, 13.7; LCMS (ESI): m/z [M + ]. Anal. Calcd For (C 32 H 25 7 O 4 ): C, 67.24; H, 4.41;, 17.15%. Found: C, 66.87; H, 4.15;, 16.95%. 2. Antibacterial assay The newly synthesized compounds (4a o) were screened for their antibacterial activity against Gram positive (Staphylococcus aureus (MTCC-96), Streptococcus pyogenes (MTCC-442), and Gram-negative bacteria Escherichia coli (MTCC-443), Pseudomonas aeruginosa (MTCC-1688) at different concentrations of 1000, 500, 200, 100, 50, 25, 12.5 µg ml -1. Several of the recently synthesized compounds (4a o) are found to exhibit moderate to excellent antimicrobial activity. On the basis of antibacterial screening results, All MTCC cultures were collected from the Institute of Microbial Technology, Chandigarh. Antibacterial activity was carried out by serial broth dilution method. [33-36] The standard strains used for the antimicrobial activity was procured from Institute of Microbial Technology, Chandigarh. The drugs which were found to be active in 8
9 primary screening were similarly diluted to obtain 100, 50, 25, 12.5 µg ml -1 concentrations. 10 μg ml -1 suspensions were further inoculated on appropriate media and growth was noted after 24 and 48 h. The lowest concentration preventing appearance of turbidity was considered as minimum inhibitory concentration (MIC, μg ml -1 ) i.e., the amount of growth from the control tube before incubation (which represents the original inoculum) was compared. A set of tubes containing only seeded broth and solvent controls were maintained under identical conditions so as to make sure that the solvent had no influence on strain growth. The standard drug used in this study was ampicillin for evaluating antibacterial activity which showed (100, 100, 250, and 100 μg ml -1 ) MIC against E. coli, P. aeruginosa, S. aureus, and S. pyogene, respectively (Table 1). 3. Antifungal assay The newly synthesized compounds (4a o) were screened for their antifungal activity against in six sets against C. albicans, A. niger and A. clavatus at various concentrations of 1000, 500, 250, and 100 μg ml -1. The compounds found to be active in primary screening were similarly diluted to obtain 200, 125, 100, 62.5, 50, 25 and 12.5 μg ml -1 concentrations for secondary screening to test in a second set of dilution against all microorganisms. Griseofulvin was used as a standard drug for antifungal activity, which shows 500, 100 and 100 μg ml -1 MIC against C. albicans, A. niger and A. clavatus, respectively (Table 1). For fungal growth, in the present protocol, we have used Sabourauds dextrose broth at 28 ºC in aerobic condition for 48 h. 9
10 4. IR, 1 H MR and Mass Spectral files of compound IR spectra of compound 4a 10
11 1 H MR spectra of compound 4a 11
12 Mass spectra of compound 4a 12
13 1 H MR spectra of compound 4b 13
14 1 H MR spectra of compound 4d H CH O 3 OH 14
15 Mass spectra of compound 4d H CH O 3 OH 15
16 1 H MR spectra of compound 4f 16
17 1 H MR spectra of compound 4g H CH O 3 O 2 17
18 1 H MR spectra of compound 4m H CH O 3 CH 3 18
19 13 C MR spectra of compound 4m H CH O 3 CH 3 19
20 Mass spectra of compound 4m H CH O 3 CH 3 20
21 1 H MR spectra of compound 4n H CH O 3 OCH 3 21
22 13 C MR spectra of compound 4n H CH O 3 OCH 3 22
23 Mass spectra of compound 4n H CH O 3 OCH 3 23
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