Synthesis of N-tetra-O-acetyl-beta-D-glucopyranosyl-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas

Carbohydr Res. 2009 Nov 23;344(17):2399-405. doi: 10.1016/j.carres.2009.09.002. Epub 2009 Sep 6.

Abstract

Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in the presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely, refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / analogs & derivatives*
  • Acetylglucosamine / chemical synthesis
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Candida albicans / drug effects
  • Enterobacter aerogenes / drug effects
  • Microbial Sensitivity Tests
  • Pyrimidines / chemical synthesis*
  • Staphylococcus epidermidis / drug effects
  • Thiourea / analogs & derivatives*
  • Thiourea / chemical synthesis

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Pyrimidines
  • Thiourea
  • Acetylglucosamine