Ketene dithioacetal mediated synthesis of 1,3,4,5-tetrasubstituted pyrazole derivatives and their biological evaluation |
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Authors: | Pravin S Bhale Babasaheb P Bandgar Sakharam B Dongare Sadanand N Shringare Dnyaneshwar M Sirsat |
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Institution: | 1. Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India;2. Department of Chemistry, Yeshwantrao Chavan Mahavidyalaya, Tuljapur, Dist-Osmanabad, Maharashtra, India;3. Department of Chemistry, A. R. A. C. S. College, Vaibhavwadi, Dist-Sindhudurg, Maharashtra, India |
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Abstract: | AbstractKetene dithioacetal mediated chemo- and regioselective synthesis of a series of novel 1,3,4,5-tetrasubstituted pyrazole derivatives (4a-l) integrated with a bioactive indole nucleus was achieved by reacting substituted 2-(1-methyl-1H-indole-3-carbonyl)-3,3-bis-(methylthio)-acrylonitrile (2) and substituted phenyl hydrazine hydrochloride (3) in the presence of a catalytic amount of anhydrous K2CO3 under reflux conditions. The structures were ascertained by 1H NMR, NOESY, 13C NMR, FT-IR, and HRMS data. In vitro cytotoxicity evaluation of the synthesized compounds against MCF 7 (breast carcinoma) and normal Vero (monkey kidney) cell lines revealed that the compound 5-(5-Bromo-1-methyl-1H-indol-3-yl)-1-(4-cyano-phenyl)-3-methylsulfanyl-1H-pyrazole-4-carbonitrile (4k) showed significant cytotoxicity against MCF 7 (GI50 = 15.6 µM) with low cytotoxicity against normal Vero cell line. Most of the synthesized compounds were also found to possess excellent anti-inflammatory and antioxidant (DPPH, NO, H2O2 and SOR) potential. |
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Keywords: | α-Aroylketene dithioacetal anti-inflammatory antioxidant breast cancer pyrazole |
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