Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
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Authors: | Maria S. Volkova Alexander M. Efremov Elena N. Bezsonova Michael D. Tsymliakov Anita I. Maksutova Maria A. Salykina Sergey E. Sosonyuk Elena F. Shevtsova Natalia A. Lozinskaya |
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Affiliation: | 1.Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia;2.Institute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences (IPAC RAS), 142432 Moscow, Russia |
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Abstract: | 2,3-Dihydroindoles are promising agents for the synthesis of new compounds with neuroprotective and antioxidant properties. Usually, these compounds are obtained by direct reduction of the corresponding indoles containing acceptor groups in the indole ring for its activation. In this work, we propose a synthetic strategy to obtain new 2,3-dihydroindole derivatives from the corresponding polyfunctional 2-oxindoles. Three methods were proposed for reduction of functional groups in the 2-oxindole and 2-chloroindole molecules using various boron hydrides. The possibility of chemoselective reduction of the nitrile group in the presence of an amide was shown. The proposed synthetic strategy can be used, for example, for the synthesis of new analogs of the endogenous hormone melatonin and other compounds with neuroprotective properties. |
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Keywords: | 2,3-dihydroindole 2-chloromelatonin chemoselective reduction melatonin nitrile reduction 2-oxindole reduction |
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