Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives

Eur J Med Chem. 2018 May 10:151:248-260. doi: 10.1016/j.ejmech.2018.03.083. Epub 2018 Mar 31.

Abstract

In the search for new antifungal agents, a novel series of fifteen hydrazine-thiazole derivatives was synthesized and assayed in vitro against six clinically important Candida and Cryptococcus species and Paracoccidioides brasiliensis. Eight compounds showed promising antifungal activity with minimum inhibitory concentration (MIC) values ranging from 0.45 to 31.2 μM, some of them being equally or more active than the drug fluconazole and amphotericin B. Active compounds were additionally tested for toxicity against human embryonic kidney (HEK-293) cells and none of them exhibited significant cytotoxicity, indicating high selectivity. Molecular modeling studies results corroborated experimental SAR results, suggesting their use in the design of new antifungal agents.

Keywords: Antifungal agents; Hydrazine-thiazoles; QSAR.

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Candida / drug effects*
  • Candidiasis / drug therapy
  • Cryptococcosis / drug therapy
  • Cryptococcus / drug effects*
  • HEK293 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Paracoccidioides / drug effects*
  • Paracoccidioidomycosis / drug therapy
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology*

Substances

  • Antifungal Agents
  • Thiazoles