Micelles catalyzed chemoselective synthesis 'in water' and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents

Bioorg Med Chem Lett. 2011 Nov 1;21(21):6398-403. doi: 10.1016/j.bmcl.2011.08.095. Epub 2011 Aug 31.

Abstract

Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent), and TBAB, a phase transfer catalyst and evaluated for their in vitro antifungal and antibacterial activity. The antifungal profile of 3, 4a, 4b, and 6 indicated that compounds 3a, 3b, 4b, 6a, and 6c have potent antifungal activity compared to clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Sporothrix schenckii, Trichophyton mentagraphytes, and Candida parapsilosis and compound 3b has been found to be a lead antifungal agent for further study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Candida / drug effects
  • Catalysis
  • Drug Evaluation, Preclinical
  • Micelles*
  • Microbial Sensitivity Tests
  • Naphthoquinones / chemistry*
  • Naphthoquinones / pharmacology*
  • Oxygen / chemistry*
  • Sporothrix / drug effects
  • Trichophyton / drug effects
  • Water

Substances

  • Antifungal Agents
  • Micelles
  • Naphthoquinones
  • Water
  • 1,4-naphthoquinone
  • Oxygen