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Synthesis of new 1,3,4-oxadiazole and benzothiazolylthioether derivatives of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-one as potential antimycobacterial agents

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Abstract

A new series of 4-[(substituted benzylidene)-3-[(5-(pyridine-4-yl)-1,3,4-oxadiazole-2-ylthio)-methyl]isoxazol-5(4H)-one (6a–g) and 4-(substituted benzylidene)-3-((benzo[d]thiazol-2-ylthio)methyl)isoxazol-5(4H)-one (8a–g) was synthesized. All the synthesized compounds were screened for antitubercular activity against Mycobacterium tuberculosis H37Ra (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743) and antibacterial activity against Escherichia coli (NCIM 2576), Pseudomonas flurescence (NCIM 2059), Staphylococcus aureus (NCIM 2602), Bacillus subtilis (NCIM 2162). Amongst the synthesized 1,3,4-oxadiazole and benzothiazoyl thioether derivatives, compounds 6b and 8b showed excellent antimycobacterial activity and compounds 6b, 8a, 8b, and 8d showed excellent antibacterial activity against all tested antibacterial strains. The synthesized compounds were further evaluated for their cytotoxic activity against the HCT 116 and HeLa cancer cell lines. The 1,3,4-oxadiazole and benzothiazoyl thioether derivatives 6a–g and 8a–g did not show cytotoxicity.

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Acknowledgements

The authors would like to express sincere thanks to Savitribai Phule Pune University, Pune and DST, New Delhi for providing financial assistance. CIF Savitribai Phule Pune University is also acknowledged for the spectral analysis.

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Authors and Affiliations

  1. Department of Chemistry, Sir Parashurambhau College, Affiliated to Savitribai Phule Pune University, Tilak Road, Pune, 411030, India

    Abhijit P. Chavan, Abhijit Shinde & Pravin C. Mhaske

  2. Department of Chemistry, HPT Arts and RYK Science College, Affiliated to Savitribai Phule Pune University, Nasik, 422005, India

    Abhijit P. Chavan & Vivek D. Bobade

  3. Department of Zoology, Modern College of Arts, Science and Commerce, Affiliated to Savitribai Phule Pune University, Shivajinagar Pune, Pune, 411005, India

    Rujuta R. Deshpande

  4. Department of Chemistry, Kirti M. Doongursee College, Affiliated to University of Mumbai, Kashinath Dhuru Road, Off. Veer Savarkar Marg, Dadar (W), Mumbai, 400028, India

    Nandkumar A. Borade

  5. CombiChemBio Resource Centre, CSIR-National Chemical Laboratory, Pune, 411008, India

    Dhiman Sarkar

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  1. Abhijit P. Chavan
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Correspondence to Pravin C. Mhaske or Vivek D. Bobade.

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Chavan, A.P., Deshpande, R.R., Borade, N.A. et al. Synthesis of new 1,3,4-oxadiazole and benzothiazolylthioether derivatives of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-one as potential antimycobacterial agents. Med Chem Res 28, 1873–1884 (2019). https://doi.org/10.1007/s00044-019-02420-7

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