Synthesis and antitubercular activity of novel 4-substituted imidazolyl-2,6-dimethyl-N3,N5-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides

Eur J Med Chem. 2009 Aug;44(8):3253-8. doi: 10.1016/j.ejmech.2009.03.027. Epub 2009 Mar 27.

Abstract

A series of 4-substituted imidazolyl-2,6-dimethyl-N(3),N(5)-bisaryl-1,4-dihydropyridine-3,5-dicarboxamides were prepared. They were screened as antitubercular agents against Mycobacterium tuberculosis H(37)Rv. Minimum inhibitory concentrations (MICs) were determined using agar proportion method. Compound 3i with 1-benzyl-2-methylthio-1H-imidazole-5-yl substituent at C-4 position and 4'-chloromophenyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring was the most potent one among the tested compounds. It was as potent as rifampicin against M. tuberculosis H(37)RV. Compound 3l also was an active antitubercular agent with the same substituent as compound 3i at the C-4 position and 3'-pyridyl group at C-3 and C-5 positions of the 1,4-dihydropyridine ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Antitubercular Agents / toxicity
  • Cell Line
  • Drug Design*
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / pharmacology*
  • Imidazoles / toxicity
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects

Substances

  • Antitubercular Agents
  • Imidazoles