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Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation

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Abstract

Searching for new active molecules against M. Bovis BCG and Mycobacterium tuberculosis (MTB) H37Ra, a focused of 1,2,3-triazoles-incorporated 2,4 thiazolidinedione conjugates have been efficiently prepared via a click chemistry approach cyclocondensation of 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) with good to promising yields. The newly synthesized compounds were tested against drug-sensitive MTB and BCG. In particular, compounds 8g, 8h, 8j and 8l are highly potent against both the strains with IC90 values in the range of 1.20–2.70 and 1.24–2.65 µg/mL, respectively. Based on the results from the antitubercular activity, SAR for the synthesized series has been developed. Most of the active compounds were non-cytotoxic against MCF-7, HCT 116 and A549 cell lines. Most active compounds were having a higher selectively index, which suggested that these compounds were highly potent.

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Authors and Affiliations

  1. J.E.S. College, Jalna, Jalna, Maharashtra, India

    Pravin S. Kulkarni, Amol U. Khandebharad, Brijmohan R. Agrawal & Swapnil R. Sarda

  2. Dr. B.A.M. University, Aurangabad, Maharashtra, India

    Sanjay N. Karale

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  1. Pravin S. Kulkarni
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Kulkarni, P.S., Karale, S.N., Khandebharad, A.U. et al. Synthesis of novel 1,2,3-triazoles bearing 2,4 thiazolidinediones conjugates and their biological evaluation. J IRAN CHEM SOC 18, 2035–2046 (2021). https://doi.org/10.1007/s13738-021-02160-9

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