Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones

Bioorg Med Chem Lett. 2010 Jan 1;20(1):193-5. doi: 10.1016/j.bmcl.2009.10.137. Epub 2009 Nov 4.

Abstract

We report here a simple entry into naphtho[2,3-d]isoxazole-4,9-dione system containing a EWG in position 3 using the readily available 2,3-dichloro-1,4-naphthoquinone and nitromethyl derivatives in the presence of base. Antifungal activity of synthesised naphthoquinones was evaluated against ATCC and PYCC reference strains of Candida. The results suggest that the naphtho[2,3-d]isoxazole-4,9-dione scaffold has the potential to be developed into novel and safe therapeutic antifungal agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Candida / drug effects
  • Isoxazoles / chemistry*
  • Microbial Sensitivity Tests
  • Naphthoquinones / chemical synthesis
  • Naphthoquinones / chemistry*
  • Naphthoquinones / pharmacology

Substances

  • Antifungal Agents
  • Isoxazoles
  • Naphthoquinones
  • 1,4-naphthoquinone