Synthesis of arylated coumarins by Suzuki-Miyaura cross-coupling. Reactions and anti-HIV activity

Bioorg Med Chem. 2016 Nov 1;24(21):5115-5126. doi: 10.1016/j.bmc.2016.08.029. Epub 2016 Sep 4.

Abstract

Arylated coumarins were prepared by site-selective Suzuki-Miyaura cross-coupling reaction of the bis(triflate) of 4-methyl-6,7-dihydroxycoumarin. Triarylated coumarins were prepared by Suzuki-Miyaura cross-coupling reactions of 3-bromo-4-methyl-2-oxo-2H-chromene-6,7-diylbis(trifluoromethanesulfonate). The in vitro anti-HIV activity of the products was investigated. Two lead structures with considerable activities were identified.

Keywords: Anti-HIV activity; Coumarins; Regioselective synthesis; Suzuki–Miyaura cross-coupling reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Cell Line, Tumor
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • HIV-1 / drug effects*
  • HIV-2 / drug effects*
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • Coumarins