Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides

Carbohydr Res. 2015 Jun 17:410:1-8. doi: 10.1016/j.carres.2015.04.002. Epub 2015 Apr 13.

Abstract

A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 μΜ), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 μM). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 μM) and low toxicity to normal cells (CC50=157.83 μM). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates.

Keywords: Antimicrobial activity; Eugenol glucosides; Triazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Anti-Infective Agents / toxicity
  • Eugenol / chemical synthesis*
  • Eugenol / pharmacology*
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glucosides / pharmacology*
  • Inhibitory Concentration 50
  • Micrococcus luteus / drug effects
  • Salmonella typhimurium / drug effects
  • Triazoles / chemistry

Substances

  • Anti-Infective Agents
  • Glucosides
  • Triazoles
  • Eugenol