A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids
We describe a novel two-step approach for the synthesis of compounds with a hydroxyl-amide group (hydroxamic acids), which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The first stage is the synthesis of <i>N&...
| Published in: | Organics |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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MDPI AG
2023-04-01
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| Online Access: | https://www.mdpi.com/2673-401X/4/2/15 |
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| author | Bogdan A. Tretyakov Svyatoslav Y. Gadomsky Alexei A. Terentiev |
| author_facet | Bogdan A. Tretyakov Svyatoslav Y. Gadomsky Alexei A. Terentiev |
| author_sort | Bogdan A. Tretyakov |
| collection | DOAJ |
| container_title | Organics |
| description | We describe a novel two-step approach for the synthesis of compounds with a hydroxyl-amide group (hydroxamic acids), which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The first stage is the synthesis of <i>N</i>-substituted succinimide via the reaction of aromatic amine or carboxylic acid hydrazide with succinic anhydride. The second step involves the imide ring opening reaction by hydroxylamine. For both stages, universal synthetic methods are developed to exclude additional purification procedures for the target compounds. Sixteen hydroxamic acids are synthesized using the developed approach. Most of the compounds are obtained for the first time. |
| format | Article |
| id | doaj-art-e38d061923ff4f2e9bd4a3d5cbad3bec |
| institution | Directory of Open Access Journals |
| issn | 2673-401X |
| language | English |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| spelling | doaj-art-e38d061923ff4f2e9bd4a3d5cbad3bec2025-08-20T01:00:41ZengMDPI AGOrganics2673-401X2023-04-014218619510.3390/org4020015A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic AcidsBogdan A. Tretyakov0Svyatoslav Y. Gadomsky1Alexei A. Terentiev2Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, Chernogolovka 142432, RussiaFederal Research Center of Problems of Chemical Physics and Medicinal Chemistry RAS, Chernogolovka 142432, RussiaWe describe a novel two-step approach for the synthesis of compounds with a hydroxyl-amide group (hydroxamic acids), which are widely known for their biological activity (histone deacetylase inhibitors, matrix metalloproteinases inhibitors and others). The first stage is the synthesis of <i>N</i>-substituted succinimide via the reaction of aromatic amine or carboxylic acid hydrazide with succinic anhydride. The second step involves the imide ring opening reaction by hydroxylamine. For both stages, universal synthetic methods are developed to exclude additional purification procedures for the target compounds. Sixteen hydroxamic acids are synthesized using the developed approach. Most of the compounds are obtained for the first time.https://www.mdpi.com/2673-401X/4/2/15<i>N</i>-substituted succinimideshydroxylaminehydroxamic acidsimide ring openingHDAC inhibitorsMMP inhibitors |
| spellingShingle | Bogdan A. Tretyakov Svyatoslav Y. Gadomsky Alexei A. Terentiev A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids <i>N</i>-substituted succinimides hydroxylamine hydroxamic acids imide ring opening HDAC inhibitors MMP inhibitors |
| title | A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids |
| title_full | A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids |
| title_fullStr | A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids |
| title_full_unstemmed | A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids |
| title_short | A Reaction of <i>N</i>-Substituted Succinimides with Hydroxylamine as a Novel Approach to the Synthesis of Hydroxamic Acids |
| title_sort | reaction of i n i substituted succinimides with hydroxylamine as a novel approach to the synthesis of hydroxamic acids |
| topic | <i>N</i>-substituted succinimides hydroxylamine hydroxamic acids imide ring opening HDAC inhibitors MMP inhibitors |
| url | https://www.mdpi.com/2673-401X/4/2/15 |
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