Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones
A series of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones (1–17) was synthesized and evaluated in vitro for its antimicrobial and anticancer activities. Results of antimicrobial screening indicated that 1-[4-[4-Chloro-pheny...
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| Format: | Article |
| Language: | English |
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Elsevier
2019-12-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535215001811 |
| _version_ | 1819097706275012608 |
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| author | Deepak Verma Pradeep Kumar Balasubramanian Narasimhan Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed |
| author_facet | Deepak Verma Pradeep Kumar Balasubramanian Narasimhan Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed |
| author_sort | Deepak Verma |
| collection | DOAJ |
| description | A series of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones (1–17) was synthesized and evaluated in vitro for its antimicrobial and anticancer activities. Results of antimicrobial screening indicated that 1-[4-[4-Chloro-phenyl)-2-[(3-nitro-phenylazo)-methyl]-benzo[b][1,4]diazepin-1-yl]-2-(2-methyl-5-nitro-phenyl amino)-ethanone (16) and 1-[4-(3,4-dimethoxy-phenyl)-2-[(4-nitro-phenylazo)-methyl]-benzo[b][1,4]diazepin-1-yl]-2-(3-nitrophenylamino)-ethanone (17) were found to be the most effective antimicrobial agents. The anticancer screening results indicated that 1-[4-(4-dimethylamino-phenyl)-2-(p-tolylazo-methyl)-benzo[b][1,4]diazepin-1-yl]-2-phenyl aminoethanone (1, IC50 = 1.42 μM/mL against HCT 116 cancer cell lines) was the most potent anticancer agent and was more potent than 5-FU. The results of QSAR studies demonstrated the importance of topological parameters, Kier’s alpha first order shape index (κα1) and valence zero order molecular connectivity index (0χv) in describing antimicrobial activity, LUMO and κα2 in describing anticancer activity of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones. Keywords: Benzodiazepines, QSAR, Antibacterial, Antifungal, Anticancer |
| first_indexed | 2024-12-22T00:19:21Z |
| format | Article |
| id | doaj.art-f331dff0dd7a49d2a49df06cab1caf4c |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-22T00:19:21Z |
| publishDate | 2019-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-f331dff0dd7a49d2a49df06cab1caf4c2022-12-21T18:45:12ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112828822896Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanonesDeepak Verma0Pradeep Kumar1Balasubramanian Narasimhan2Kalavathy Ramasamy3Vasudevan Mani4Rakesh Kumar Mishra5Abu Bakar Abdul Majeed6Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, IndiaFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, IndiaFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, India; Corresponding author. Mobile: +91 9416649342.Collaborative Drug Discovery Research Group, Faculty of Pharmacy, Campus Puncak Alam, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, MalaysiaBrain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, MalaysiaBrain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, MalaysiaBrain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam, Universiti Teknologi MARA (UiTM), 42300 Bandar Puncak Alam, Selangor, MalaysiaA series of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones (1–17) was synthesized and evaluated in vitro for its antimicrobial and anticancer activities. Results of antimicrobial screening indicated that 1-[4-[4-Chloro-phenyl)-2-[(3-nitro-phenylazo)-methyl]-benzo[b][1,4]diazepin-1-yl]-2-(2-methyl-5-nitro-phenyl amino)-ethanone (16) and 1-[4-(3,4-dimethoxy-phenyl)-2-[(4-nitro-phenylazo)-methyl]-benzo[b][1,4]diazepin-1-yl]-2-(3-nitrophenylamino)-ethanone (17) were found to be the most effective antimicrobial agents. The anticancer screening results indicated that 1-[4-(4-dimethylamino-phenyl)-2-(p-tolylazo-methyl)-benzo[b][1,4]diazepin-1-yl]-2-phenyl aminoethanone (1, IC50 = 1.42 μM/mL against HCT 116 cancer cell lines) was the most potent anticancer agent and was more potent than 5-FU. The results of QSAR studies demonstrated the importance of topological parameters, Kier’s alpha first order shape index (κα1) and valence zero order molecular connectivity index (0χv) in describing antimicrobial activity, LUMO and κα2 in describing anticancer activity of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones. Keywords: Benzodiazepines, QSAR, Antibacterial, Antifungal, Anticancerhttp://www.sciencedirect.com/science/article/pii/S1878535215001811 |
| spellingShingle | Deepak Verma Pradeep Kumar Balasubramanian Narasimhan Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones Arabian Journal of Chemistry |
| title | Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones |
| title_full | Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones |
| title_fullStr | Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones |
| title_full_unstemmed | Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones |
| title_short | Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones |
| title_sort | synthesis antimicrobial anticancer and qsar studies of 1 4 substituted phenyl 2 substituted phenyl azomethyl benzo b 1 4 diazepin 1 yl 2 substituted phenylaminoethanones |
| url | http://www.sciencedirect.com/science/article/pii/S1878535215001811 |
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