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Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction

8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. The Mannich reaction is one of the most easily...

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Autores principales: Csuvik, Oszkár, Szatmári, István
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10177806/
https://www.ncbi.nlm.nih.gov/pubmed/37175622
http://dx.doi.org/10.3390/ijms24097915
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author Csuvik, Oszkár
Szatmári, István
author_facet Csuvik, Oszkár
Szatmári, István
author_sort Csuvik, Oszkár
collection PubMed
description 8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. The Mannich reaction is one of the most easily implementable examples, which requires mild reaction conditions and simple chemical reagents. The three components of the Mannich reaction are a primary or secondary amine, an aldehyde and a compound having a hydrogen with pronounced activity. In the modified Mannich reaction, naphthol or a nitrogen-containing naphthol analogue (e.g., 8-hydroxyquinoline) is utilised as the active hydrogen provider compound, thus affording the formation of aminoalkylated products. The amine component can be ammonia and primary or secondary amines. The aldehyde component is highly variable, including aliphatic and aromatic aldehydes. Based on the pharmacological relevance of aminomethylated 8-hydroxyquinolines, this review summarises their syntheses via the modified Mannich reaction starting from 8-hydroxyquinoline, formaldehyde and various amines.
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spelling pubmed-101778062023-05-13 Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction Csuvik, Oszkár Szatmári, István Int J Mol Sci Review 8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. The Mannich reaction is one of the most easily implementable examples, which requires mild reaction conditions and simple chemical reagents. The three components of the Mannich reaction are a primary or secondary amine, an aldehyde and a compound having a hydrogen with pronounced activity. In the modified Mannich reaction, naphthol or a nitrogen-containing naphthol analogue (e.g., 8-hydroxyquinoline) is utilised as the active hydrogen provider compound, thus affording the formation of aminoalkylated products. The amine component can be ammonia and primary or secondary amines. The aldehyde component is highly variable, including aliphatic and aromatic aldehydes. Based on the pharmacological relevance of aminomethylated 8-hydroxyquinolines, this review summarises their syntheses via the modified Mannich reaction starting from 8-hydroxyquinoline, formaldehyde and various amines. MDPI 2023-04-26 /pmc/articles/PMC10177806/ /pubmed/37175622 http://dx.doi.org/10.3390/ijms24097915 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Csuvik, Oszkár
Szatmári, István
Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title_full Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title_fullStr Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title_full_unstemmed Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title_short Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction
title_sort synthesis of bioactive aminomethylated 8-hydroxyquinolines via the modified mannich reaction
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10177806/
https://www.ncbi.nlm.nih.gov/pubmed/37175622
http://dx.doi.org/10.3390/ijms24097915
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