Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity.

Autor: Volkova MS; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Efremov AM; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; 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., Bezsonova EN; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Tsymliakov MD; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; 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., Maksutova AI; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Salykina MA; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Sosonyuk SE; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia., Shevtsova EF; 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., Lozinskaya NA; Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia.; 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.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2022 Nov 02; Vol. 27 (21). Date of Electronic Publication: 2022 Nov 02.
DOI: 10.3390/molecules27217462
Abstrakt: 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.
Databáze: MEDLINE
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