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Microwave-assisted synthesis of benzenesulfonohydrazide and benzenesulfonamide cyclic imide hybrid molecules and their evaluation for anticancer activity

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Abstract

4-Methyl benzenesulfonohydrazide (1a) and 4-methoxy benzenesulfonohydrazide (1b) on condensation with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione under microwave irradiation condition gave corresponding condensation products 2a,b; 3a,b; 4a,b and 5a,b, respectively, in good yields. Microwave-assisted condensation of 4-amino-N-(thiazol-2-yl)benzenesulfonamide (6a), 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (6b) and 4-amino-N-(4-methyl pyrimidin-2-yl)benzenesulfonamide (6c) with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione gave corresponding condensation products 7a–c, 8a–c, 9a–c and 10a–c, respectively, in good yields. All these compounds, i.e., 2a,b; 3a,b; 4a,b; 5a,b; 7a–c; 8a–c; 9a–c and 10a–c, were screened for in vitro anticancer activity against five human cancer cell lines, i.e., breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1) and liver (Hep G2). Compounds 7c and 9c exhibited good anticancer activity against ovary (PA-1) (IC50 value 8.12 ± 1.83 µM) and liver (Hep G2) (IC50 value 4 ± 1.9 µM) cancer cell lines, respectively.

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Acknowledgments

We are thankful to technical staff of the Chemistry Department, IIT Roorkee, for spectroscopic studies and elemental analysis. Thanks are also due to Head IIC for providing NMR facility. Mr. Anuj Kumar is thankful to MHRD, New Delhi, for financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology-Roorkee, Roorkee, Uttrakhand, 247667, India

    Anuj Kumar, S. M. Sondhi & Anuj Sharma

  2. Department of Biotechnology, Indian Institute of Technology-Roorkee, Roorkee, Uttrakhand, 247667, India

    Nikhil Kumar & Partha Roy

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  1. Anuj Kumar
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Correspondence to Anuj Sharma.

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Kumar, A., Kumar, N., Roy, P. et al. Microwave-assisted synthesis of benzenesulfonohydrazide and benzenesulfonamide cyclic imide hybrid molecules and their evaluation for anticancer activity. Med Chem Res 24, 3760–3771 (2015). https://doi.org/10.1007/s00044-015-1414-9

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