Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity

Roman O. Iakovenko, Andrea Chicca, Daniela Nieri, Ines Reynoso-Moreno, Jürg Gertsch, Mikhail Krasavin, Aleksander V. Vasilyev

Research output

5 Citations (Scopus)

Abstract

A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB 1 or CB 2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds.

Original languageEnglish
Pages (from-to)624-632
JournalTetrahedron
Volume75
Issue number5
Early online date24 Dec 2018
DOIs
Publication statusPublished - Feb 2019

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity'. Together they form a unique fingerprint.

  • Cite this