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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

  • Vikas Shinde
  • Pramod MahulikarEmail author
  • Pravin C. MhaskeEmail author
  • Shakti Chakraborty
  • Amit Choudhari
  • Siddharth Phalle
  • Prafulla Choudhari
  • Dhiman Sarkar
Original Research
  • 18 Downloads

Abstract

A new series of 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives, 6aw have been synthesized by click reaction of substituted benzylazide, 5a−d with 5-ethynyl-4-methyl-2-substituted phenylthiazole, 4af. 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.

Keywords

Thiazole 1,2,3-Triazole Ohira−Bestmann reagent Antitubercular activity Molecular docking 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Vikas Shinde
    • 1
  • Pramod Mahulikar
    • 1
    Email author
  • Pravin C. Mhaske
    • 2
    Email author
  • Shakti Chakraborty
    • 3
  • Amit Choudhari
    • 3
  • Siddharth Phalle
    • 4
  • Prafulla Choudhari
    • 4
  • Dhiman Sarkar
    • 3
  1. 1.School of Chemical SciencesNorth Maharashtra UniversityJalgaonIndia
  2. 2.Post Graduate Department of Chemistry, S.P. Mandali’s Sir Parashurambhau CollegeSavitribai Phule Pune UniversityPuneIndia
  3. 3.CombiChemBio Resource CentreCSIR-National Chemical LaboratoryPuneIndia
  4. 4.Department of Pharmaceutical ChemistryBharati Vidyapeeth College of PharmacyKolhapurIndia

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