Unusual transformation of substituted-3-formylchromones to pyrimidine analogues: synthesis and antimicrobial activities of 5-(o-hydroxyaroyl)pyrimidines

Bioorg Med Chem Lett. 2013 Nov 15;23(22):6093-6. doi: 10.1016/j.bmcl.2013.09.024. Epub 2013 Sep 17.

Abstract

Substituted-3-formylchromones (4a-e) on reaction with 1,3-bis-dimethylaminomethylene-thiourea (5) in refluxing toluene solution give novel substituted 5-(o-hydroxyaroyl)pyrimidines (6a-e) in high yields. A mechanistic rationalization of the formation of products (6a-e) is proffered. Antimicrobial activities of all the synthesized compounds (6a-e) were evaluated against various fungal and bacterial strains. Compound 6d display significant antifungal activity (MIC 15) against Geotrichum candidum in comparison fluconazole used as positive control. Some of the compounds also display good antibacterial activity. Cytotoxic profile of compound 6d against HeLa cells indicates that at concentration (20 μM) no significant cell death (~2%) was observed.

Keywords: 3-Formylchromones; Antibacterial activities; Antifungal activities; Azadienes; Pyrimidines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Candida / drug effects
  • Chromones / chemical synthesis*
  • Chromones / chemistry
  • Chromones / pharmacology*
  • Geotrichum / drug effects
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Chromones
  • Pyrimidines
  • formylchromone