Synthesis and biological activity of novel 1-substituted phenyl-4-[N-[(2'-morpholinothoxy)phenyl]aminomethyl]-1H-1,2,3-triazoles

Chem Biol Drug Des. 2011 Oct;78(4):695-9. doi: 10.1111/j.1747-0285.2011.01172.x. Epub 2011 Aug 3.

Abstract

In an attempt to search for potent antifungal agents, a series of novel 1-substituted phenyl-4-[N-[(2'-morpholinothoxy)phenyl]aminomethyl]-1H-1,2,3-triazoles 5a-m was designed and synthesized via Huisgen cycloaddition reaction between various (2-morpholinoethoxy)-N-(prop-2-ynyl)aniline and different azidobenzene. Their chemical structures were characterized by (1) H NMR and elemental analysis. A cleaner reaction with milder conditions and satisfactory yields was observed in the micorwave-assisted synthesis of 4a-c. The fungicidal activity of some target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Cercospora arachidicola and Gibberella zeae at 50 μg/mL. The bioassay results indicated that some compounds exhibited moderate fungicidal activities. Furthermore, compound 5h displayed equal activity to the positive control compounds against Alternaria solani.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Drug Design
  • Fungi / drug effects*
  • Humans
  • Mycoses / drug therapy
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology*

Substances

  • Antifungal Agents
  • Triazoles