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[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

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Abstract

We have described a highly efficient, safer protocol for the synthesis of 5-arylidene-rhodanine conjugates catalyzed by Bronsted acidic ionic liquid [Et3NH][HSO4] in excellent yields. The protocol offers cost-effective, environmentally benign, solvent-free conditions and recycle–reuse of the catalyst. The synthesized 5-arylidene-rhodanine conjugates were characterized on the basis of 1H NMR, 13C NMR and HRMS spectral data. A series of 5-arylidene-rhodanine derivatives 3a–h, 4a–h were synthesized and evaluated for their in vitro antitubercular activity against dormant Mycobacterium tuberculosis H37Ra and M. bovis BCG strains. Moreover, compounds 3a, 3b, 3e, 3f, 3g, 3h and 4f exhibited good antitubercular activity and were also evaluated for anti-proliferative activity against MCF-7, A549 and HCT116 cell lines using modified MTT assay and found to be noncytotoxic. Compounds 3a–h and 4f were further screened for their antibacterial activity against four bacteria strains to assess their selectivity towards M. tuberculosis. Furthermore, in silico ADME prediction of all the tested compounds followed the criteria for orally active drug and, therefore, these compounds may have a good potential for eventual development as oral agents.

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Acknowledgments

The authors D.D.S and. M.H.S. are very grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, for the award of a Senior Research Fellowship. They are also grateful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431 004, India, for providing the laboratory facility.

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Authors and Affiliations

  1. UGC-SAP and DST-FIST Sponsored, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431 004, India

    Dnyaneshwar D. Subhedar, Mubarak H. Shaikh & Bapurao B. Shingate

  2. Combichem Bioresource Center, Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune, 411 008, India

    Laxman Nawale, Amar Yeware & Dhiman Sarkar

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  1. Dnyaneshwar D. Subhedar
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Subhedar, D.D., Shaikh, M.H., Nawale, L. et al. [Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity. Res Chem Intermed 42, 6607–6626 (2016). https://doi.org/10.1007/s11164-016-2484-0

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