Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides
A series of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1–32) was synthesized and evaluated for its in vitro antimicrobial, antiviral and cytotoxic activities. Antimicrobial results indicated that compounds (11) and (18) were found to be the most e...
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| Format: | Article |
| Language: | English |
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Elsevier
2014-09-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535212002961 |
| _version_ | 1818341448539439104 |
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| author | Mahesh Kumar Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed Erik De Clercq Balasubramanian Narasimhan |
| author_facet | Mahesh Kumar Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed Erik De Clercq Balasubramanian Narasimhan |
| author_sort | Mahesh Kumar |
| collection | DOAJ |
| description | A series of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1–32) was synthesized and evaluated for its in vitro antimicrobial, antiviral and cytotoxic activities. Antimicrobial results indicated that compounds (11) and (18) were found to be the most effective ones. In general, the synthesized compounds were bacteriostatic and fungistatic in their action. The cytotoxic screening results indicated that the compounds were less active than the standard drug 5-fluorouracil (5-FU). None of the compounds inhibited viral replication at subtoxic concentrations. In general, the presence of a pyrimidine ring with electron releasing groups and an ortho- and para-substituted benzoyl moiety favored antimicrobial activities. The results of QSAR studies demonstrated the importance of topological parameters, valence zero order molecular connectivity index (0χv) and valence first order molecular connectivity index (1χv) in describing the antimicrobial activity of synthesized compounds. |
| first_indexed | 2024-12-13T15:58:57Z |
| format | Article |
| id | doaj.art-1a0d0ab4a3014a8bbb11bc9f3443a904 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-13T15:58:57Z |
| publishDate | 2014-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-1a0d0ab4a3014a8bbb11bc9f3443a9042022-12-21T23:39:13ZengElsevierArabian Journal of Chemistry1878-53522014-09-017439640810.1016/j.arabjc.2012.12.005Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamidesMahesh Kumar0Kalavathy Ramasamy1Vasudevan Mani2Rakesh Kumar Mishra3Abu Bakar Abdul Majeed4Erik De Clercq5Balasubramanian Narasimhan6Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, IndiaCollaborative 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, MalaysiaLaboratory of Virology & Chemotherapy, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, BelgiumFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, IndiaA series of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzenesulfonamide derivatives (1–32) was synthesized and evaluated for its in vitro antimicrobial, antiviral and cytotoxic activities. Antimicrobial results indicated that compounds (11) and (18) were found to be the most effective ones. In general, the synthesized compounds were bacteriostatic and fungistatic in their action. The cytotoxic screening results indicated that the compounds were less active than the standard drug 5-fluorouracil (5-FU). None of the compounds inhibited viral replication at subtoxic concentrations. In general, the presence of a pyrimidine ring with electron releasing groups and an ortho- and para-substituted benzoyl moiety favored antimicrobial activities. The results of QSAR studies demonstrated the importance of topological parameters, valence zero order molecular connectivity index (0χv) and valence first order molecular connectivity index (1χv) in describing the antimicrobial activity of synthesized compounds.http://www.sciencedirect.com/science/article/pii/S1878535212002961IsatinQSARAntimicrobialAntiviralAnticancer/cytotoxic |
| spellingShingle | Mahesh Kumar Kalavathy Ramasamy Vasudevan Mani Rakesh Kumar Mishra Abu Bakar Abdul Majeed Erik De Clercq Balasubramanian Narasimhan Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides Arabian Journal of Chemistry Isatin QSAR Antimicrobial Antiviral Anticancer/cytotoxic |
| title | Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides |
| title_full | Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides |
| title_fullStr | Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides |
| title_full_unstemmed | Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides |
| title_short | Synthesis, antimicrobial, anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substituted benzene sulfonamides |
| title_sort | synthesis antimicrobial anticancer antiviral evaluation and qsar studies of 4 1 aryl 2 oxo 1 2 dihydro indol 3 ylideneamino n substituted benzene sulfonamides |
| topic | Isatin QSAR Antimicrobial Antiviral Anticancer/cytotoxic |
| url | http://www.sciencedirect.com/science/article/pii/S1878535212002961 |
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