Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity
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 propos...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7462 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Maria S. Volkova |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T18:48:05Z |
| format | Article |
| id | doaj.art-8dbcec8864c348d69da9895ec2b97a5d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:48:05Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8dbcec8864c348d69da9895ec2b97a5d2023-11-24T06:04:39ZengMDPI AGMolecules1420-30492022-11-012721746210.3390/molecules27217462Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding AffinityMaria S. Volkova0Alexander M. Efremov1Elena N. Bezsonova2Michael D. Tsymliakov3Anita I. Maksutova4Maria A. Salykina5Sergey E. Sosonyuk6Elena F. Shevtsova7Natalia A. Lozinskaya8Department of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaInstitute of Physiologically Active Compounds at Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences (IPAC RAS), 142432 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, 119991 Moscow, Russia2,3-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.https://www.mdpi.com/1420-3049/27/21/74622,3-dihydroindole2-chloromelatoninchemoselective reductionmelatoninnitrile reduction2-oxindole reduction |
| spellingShingle | 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 Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity Molecules 2,3-dihydroindole 2-chloromelatonin chemoselective reduction melatonin nitrile reduction 2-oxindole reduction |
| title | Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
| title_full | Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
| title_fullStr | Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
| title_full_unstemmed | Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
| title_short | Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity |
| title_sort | synthesis of new 2 3 dihydroindole derivatives and evaluation of their melatonin receptor binding affinity |
| topic | 2,3-dihydroindole 2-chloromelatonin chemoselective reduction melatonin nitrile reduction 2-oxindole reduction |
| url | https://www.mdpi.com/1420-3049/27/21/7462 |
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