Mode of action and quantitative structure-activity correlations of tuberculostatic drugs of the isonicotinic acid hydrazide type

J Med Chem. 1976 Apr;19(4):483-92. doi: 10.1021/jm00226a007.

Abstract

Quantitative structure-activity studies have been performed for a series of 2-substituted isonicotinic acid hydrazides by correlating electronic, steric, and lipophilic properties of the substituents with the biological activity date (MIC) from serial dilution tests with Mycobacterium tuberculosis (strain H 37 Rv). The reaction rates for the quaternization of 2-substituted pyridines with methyl iodide were also determined. The rate constants show a similar dependence on the steric and electronic effects of the substituents as the antibacterial activities of the corresponding pyridine-4-carboxylic acid hydrazides. The obtained correlations give evidence that the reactivity of the pyridine nitrogen atom is essential for the biological activity of 2-substituted isonicotinic acid hydrazides and seem to support the hypothesis that isonicotinic acid derivatives are incorporated into an NAD analogue.

MeSH terms

  • Antitubercular Agents / chemical synthesis
  • Antitubercular Agents / pharmacology*
  • Isoniazid / analogs & derivatives*
  • Isoniazid / chemical synthesis
  • Isoniazid / pharmacology
  • Kinetics
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects
  • Regression Analysis
  • Structure-Activity Relationship

Substances

  • Antitubercular Agents
  • Isoniazid