Design, synthesis, and structure-activity relationship studies of benzothiazole derivatives as antifungal agents

Eur J Med Chem. 2016 Nov 10:123:514-522. doi: 10.1016/j.ejmech.2016.07.067. Epub 2016 Jul 29.

Abstract

A series of compounds with benzothiazole and amide-imidazole scaffolds were designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. The antifungal activity of these compounds was evaluated in vitro, and their structure-activity relationships (SARs) were evaluated. The synthesized compounds showed excellent inhibitory activity against Candida albicans and Cryptococcus neoformans. The most potent compounds 14o, 14p, and 14r exhibited potent activity, with minimum inhibitory concentration (MIC) values in the range of 0.125-2 μg/mL. Preliminary mechanism studies revealed that the compound 14p might act by inhibiting the CYP51 of Candida albicans. The SARs and binding mode established in this study are useful for further lead optimization.

Keywords: Antifungal activity; Azole antifungals; CYP51; Structure-activity relationship.

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology*
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Benzothiazoles / metabolism
  • Benzothiazoles / pharmacology*
  • Candida albicans / drug effects
  • Catalytic Domain
  • Cryptococcus neoformans / drug effects
  • Drug Design*
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Saccharomyces cerevisiae / enzymology
  • Sterol 14-Demethylase / chemistry
  • Sterol 14-Demethylase / metabolism
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Benzothiazoles
  • Sterol 14-Demethylase