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Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives

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Abstract

A new series of 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives, 6a−w have been synthesized by click reaction of substituted benzylazide, 5a−d with 5-ethynyl-4-methyl-2-substituted phenylthiazole, 4a−f. The starting compounds 4-ethynyl-2-substituted phenylthiazole (4a−f) were synthesized from the corresponding thiazole aldehyde by using the Ohira−Bestmann reagent. The structure of the synthesized compounds was determined by spectral analysis. All the synthesized compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB, ATCC 25177). Most of the synthesized compounds reported good activity against M. tuberculosis H37Ra strain with IC50 range of 0.58−8.23 µg/mL. Compounds 6g and 6k reported good antitubercular activity with MIC90 values of 4.71 and 2.22 µg/mL, respectively. Potential antimycobacterial activity suggested that these compounds could serve as good lead compounds for further optimization and development of a newer antitubercular candidate.

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Acknowledgements

The authors would like to thank CSIR-NCL, Pune for supporting the biological activity. Central Analysis facility, Savitribai Phule Pune University, Pune is also acknowledged for the spectral analysis.

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Authors and Affiliations

  1. School of Chemical Sciences, North Maharashtra University, Jalgaon, Maharashtra, India

    Vikas Shinde & Pramod Mahulikar

  2. Post Graduate Department of Chemistry, S.P. Mandali’s Sir Parashurambhau College, Savitribai Phule Pune University, Tilak Road, Pune, Maharashtra, 411030, India

    Pravin C. Mhaske

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

    Shakti Chakraborty, Amit Choudhari & Dhiman Sarkar

  4. Department of Pharmaceutical Chemistry, Bharati Vidyapeeth College of Pharmacy, Kolhapur, Maharashtra, 413016, India

    Siddharth Phalle & Prafulla Choudhari

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  1. Vikas Shinde
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Shinde, V., Mahulikar, P., Mhaske, P.C. et al. Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives. Med Chem Res 28, 805–819 (2019). https://doi.org/10.1007/s00044-019-02310-y

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