A new and efficient method for the synthesis of novel 3-acetyl coumarins oxadiazoles derivatives with expected biological activity

Molecules. 2014 Jan 14;19(1):911-24. doi: 10.3390/molecules19010911.

Abstract

This paper presents the design of some novel 3-acetylcoumarin derivatives, based on minimal inhibitory concentration values (MICs) previously obtained against some microorganism cultures, Gram positive and negative bacteria and fungi. Some of these molecules exhibited antibacterial activity against S. aureus, comparable to that of the standard used (impinem). The in vitro antioxidant activities of the novel 3-acetylcoumarin oxadiazoles were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity method. The compounds 5c,d proved to be the most active, showing the highest capacity to deplete the DPPH radicals. Structure elucidation of the products has been accomplished on the basis of IR, 1H-NMR, 13C-NMR, NOESY and HMBC NMR data.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Benzothiazoles / chemistry
  • Biphenyl Compounds / chemistry
  • Coumarins / chemical synthesis*
  • Coumarins / pharmacology
  • Escherichia coli / drug effects
  • Fluconazole / pharmacology
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / pharmacology
  • Free Radicals / chemistry
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacology
  • Picrates / chemistry
  • Salmonella typhi / drug effects
  • Shigella flexneri / drug effects
  • Staphylococcus aureus / drug effects
  • Sulfonic Acids / chemistry

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzothiazoles
  • Biphenyl Compounds
  • Coumarins
  • Free Radical Scavengers
  • Free Radicals
  • Oxadiazoles
  • Picrates
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • 3-acetylcoumarin
  • Fluconazole
  • 1,1-diphenyl-2-picrylhydrazyl