Diaryloxy methano phenanthrenes: a new class of antituberculosis agents

Bioorg Med Chem. 2004 Oct 15;12(20):5269-76. doi: 10.1016/j.bmc.2004.07.058.

Abstract

A new series of diaryloxy methano phenanthrenes were prepared through tertiary-aminoalkylations of [(methoxy-phenyl)-phenanthren-9-yl-methyl]-phenols obtained from Friedel-Crafts alkylations on (methoxy-phenyl)-phenanthren-9-yl-methanols. These series of compounds were evaluated against Mycobacterium tuberculosis H37Rv and showed the desired activity in the range of 6.25 microg/mL in vitro. One of the compound 12j protects the mice from the challenge of M. tuberculosis in vivo, as 30% of the mice were survived at treatment of 50 mg/kg body weight.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / pharmacology*
  • Antitubercular Agents / therapeutic use
  • Female
  • Mice
  • Mycobacterium tuberculosis / drug effects*
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / pharmacology*
  • Phenanthrenes / therapeutic use
  • Tuberculosis / drug therapy

Substances

  • Antitubercular Agents
  • Phenanthrenes