A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis

Eur J Med Chem. 2009 May;44(5):2334-7. doi: 10.1016/j.ejmech.2008.06.014. Epub 2008 Jun 26.

Abstract

We report here an alternative to the MCPBA or ozonolysis-based oxidation methods of quinoxaline-featuring compounds prepared from beta-lapachones. The use of peracetic acid allowed a simple preparation of the corresponding macrolactones by cleavage of the ring system. These lactones were evaluated for their antimycobacterial potential and compound 4 turned out to have an MIC of 0.62 microg per mL on Mycocabteriumtuberculosis H37Rv. These results justify further research into its value as a potential lead for an original treatment of tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Lactones / chemical synthesis*
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects*
  • Oxidation-Reduction
  • Phenazines / chemistry*
  • Quinoxalines
  • Structure-Activity Relationship

Substances

  • Antitubercular Agents
  • Lactones
  • Phenazines
  • Quinoxalines