Synthesis and antibacterial activity of new symmetric polyoxygenated dibenzofurans

Eur J Med Chem. 2017 Dec 1:141:178-187. doi: 10.1016/j.ejmech.2017.09.062. Epub 2017 Oct 3.

Abstract

A series of symmetric polyoxygenated dibenzofurans with 2-methylbutyril moieties at C-4 and C-6 were obtained from commercial phloroglucinol through a sequence of reactions that include monoacylation, iodination, Suzuki-Miyaura coupling, oxidative dimerization and cyclization. Some of the compounds obtained were active against Gram-positive bacteria, including multiresistant Staphylococcus aureus clinical isolates. The dibenzofuran 28 with propyl chains at C-2 and C-8 exhibited the best antibacterial activity with values comparable to those of the natural dibenzofuran achyrofuran. From the obtained results some structure-activity relationships were outlined.

Keywords: Antibacterial; Dibenzofurans.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Dose-Response Relationship, Drug
  • Enterococcus faecalis / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Benzofurans
  • dibenzofuran