Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

Bioorg Med Chem. 2013 Nov 15;21(22):6910-4. doi: 10.1016/j.bmc.2013.09.034. Epub 2013 Sep 20.

Abstract

This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity.

Keywords: Antimycobacterial activity; Fatty acids; INH-derivatives; Mycobacterium tuberculosis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Drug Resistance, Bacterial / drug effects
  • Fatty Acids / chemistry*
  • Isoniazid / analogs & derivatives*
  • Isoniazid / chemical synthesis
  • Isoniazid / pharmacology*
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects*
  • Rifampin / pharmacology

Substances

  • Antitubercular Agents
  • Fatty Acids
  • Isoniazid
  • Rifampin