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.
Aws M Hamdy  1 ,  Zien Khaddour  2 ,  Najim A Al-Masoudi  3 ,  Qamar Rahman  4 ,  Christian Hering-Junghans  2 ,  Alexander Villinger  2 ,  Peter Langer  5
Affiliations
  • 1. Institute für Chemie, Universitat Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany; Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq.
  • 2. Institute für Chemie, Universitat Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany.
  • 3. Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq.
  • 4. Institute für Chemie, Universitat Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany; Amity University, Lucknow Campus, Viraj Khand-5, Gomti Nagar, Lucknow 226010, India.
  • 5. Institute für Chemie, Universitat Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany; Leibniz-Institute für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany.
PMID: 27647368 DOI: 10.1016/j.bmc.2016.08.029
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.