Synthesis and antifungal properties of N-[(1,1'-biphenyl)-4-ylmethyl]-1H-imidazol-1-amine derivatives

Farmaco. 2002 Dec;57(12):1015-8. doi: 10.1016/s0014-827x(02)01294-6.

Abstract

In the course of a study on 1H-imidazol-1-amine derivatives as antifungal agents, we found that N-[(1,1'-biphenyl)-4-ylmethyl]-N-[(2,4-dichlorophenyl)methyl]-1H-imidazol-1-amine (1a) exhibited promising activities. In order to explore more in detail the structure-activity relationship of this new class of antifungal agents, we report now the synthesis and the biological activity of new analogues (1b-k) of compound 1a. The synthesis was performed using N-[(1,1'-biphenyl)-4-ylmethyl]-1H-imidazol-1-amine as starting material which was reacted with the proper arylmethyl halide. Most of the newly synthesized imidazolamines exhibited both fungal growth inhibition activity and cellular selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Antifungal Agents / toxicity
  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / pharmacology
  • Biphenyl Compounds / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology
  • Imidazoles / toxicity
  • Microbial Sensitivity Tests
  • Mitosporic Fungi / drug effects

Substances

  • Antifungal Agents
  • Biphenyl Compounds
  • Imidazoles
  • N-((1,1'-biphenyl)-4-ylmethyl)-1H-imidazol-1-amine