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Design, synthesis and biological evaluation of novel N,4-diphenylthiazol-2-amine derivatives

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Abstract

Novel N,4-diphenylthiazol-2-amine derivatives were designed and synthesized employing Hantzsch method. The three-step reaction involved in the synthesis occurred at a faster rate with excellent yields in eco-friendly conditions. The synthesized derivatives were characterized by spectral techniques such as 1H NMR, 13C NMR, FT-IR and GCMS. Single-crystal X-ray diffraction studies also confirmed the formation of title compounds. These compounds were evaluated in vitro for their antimicrobial and anti-inflammatory activities. The results demonstrated that most of the tested compounds showed potent antifungal activity. Interestingly, these compounds also exhibited good anti-inflammatory and moderate antibacterial activity towards sensitive as well as resistant bacterial strains. In silico studies depicted their good binding affinity profile against S. aureus (PDB ID: 1AD4) and C. albicans (PDB ID: 1AI9).

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Acknowledgements

We are thankful to the University Scientific Instruments Centre (USIC and SAIF), Karnatak University, Dharwad for providing the spectral data, DST-INSPIRE, New Delhi, India, for providing financial support under DST/INSPIRE Fellowship/2016/IF160657 and DST-PURSE PHASE-II program for providing necessary facilities. One of the authors MSN is thankful to UGC-SRF for financial support.

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Correspondence to Imtiyaz Ahmed M. Khazi.

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Nadaf, A.A., Barretto, D.A., Najare, M.S. et al. Design, synthesis and biological evaluation of novel N,4-diphenylthiazol-2-amine derivatives. Med Chem Res 29, 442–458 (2020). https://doi.org/10.1007/s00044-019-02495-2

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Keywords

  • N,4-diphenylthiazol-2-amine
  • Antimicrobial
  • Anti-inflammatory
  • Ciprofloxacin
  • Fluconazole
  • Protein denaturation assay