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Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

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Abstract

A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 µM).

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Acknowledgments

The authors thank Department of Chemistry, VNSGU, Surat, for providing necessary research facilities and Atul Limited, Atul, for providing some free chemical samples. One of the authors, Faiyazalam M. Shaikh is also thankful to University Grants Commission (UGC), New Delhi, for awarding Maulana Azad National Fellowship [F1-17.1/2010/MANF-MUS-GUJ-7007/(SA-III/Website)].

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Authors and Affiliations

  1. Research Laboratory, Department of Chemistry, Veer Narmad South Gujarat University, Udhana-Magdalla Road, Surat, 395 007, Gujarat, India

    Faiyazalam M. Shaikh & Navin B. Patel

  2. Dipartimento di Scienze e Tecnologie Biomediche, Sezione di Microbiologia e Virologia Generale e Biotecnologie Microbiche, Cittadella Universitaria, SS 554 km 4.500, 09042, Monserrato, CA, Italy

    Giuseppina Sanna, Bernardetta Busonera & Paolo La Colla

  3. Microcare Laboratory and Tuberculosis Diagnosis and Research Centre, Surat, Gujarat, India

    Dhanji P. Rajani

Authors
  1. Faiyazalam M. Shaikh
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  2. Navin B. Patel
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  3. Giuseppina Sanna
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  4. Bernardetta Busonera
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  5. Paolo La Colla
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Correspondence to Navin B. Patel.

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Shaikh, F.M., Patel, N.B., Sanna, G. et al. Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities. Med Chem Res 24, 3129–3142 (2015). https://doi.org/10.1007/s00044-015-1358-0

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