A Reaction of N-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 N-substitut...

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Bibliographic Details
Published in:Organics (Basel) 2023-06, Vol.4 (2), p.186-195
Main Authors: Tretyakov, Bogdan A., Gadomsky, Svyatoslav Y., Terentiev, Alexei A.
Format: Article
Language:English
Subjects:
Acids
Ammonia
HDAC inhibitors
hydroxamic acids
hydroxylamine
imide ring opening
MMP inhibitors
N-substituted succinimides
Phenols
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Summary: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 N-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.
ISSN:2673-401X
2673-401X
DOI:10.3390/org4020015