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Synthesis of various arylated trifluoromethyl substituted indanes and indenes,and study of their biological activity |
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| Authors: | Roman O. Iakovenko Andrea Chicca Daniela Nieri Ines Reynoso-Moreno Jürg Gertsch Mikhail Krasavin Aleksander V. Vasilyev |
| Affiliation: | 1. Institute of Chemistry, Saint-Petersburg State University, Universitetsky pr. 26, 198504, Petrodvorets, Saint-Petersburg, Russia;2. St Petersburg National Research University of Information Technologies, Mechanics and Optics, Kronverkskiy pr. 49, 197101, Saint-Petersburg, Russia;3. Institute of Biochemistry and Molecular Medicine, NCCR TransCure, University of Bern, Bühlstrasse 28, 3012, Bern, Switzerland;4. Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per. 5, Saint Petersburg, 194021, Russia |
| 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 CB1 or CB2 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. |
| Keywords: | Trifluoromethyl group Indanes Indenes Biological activity |
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