Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases

KYNAs, a compound with endogenous neuroprotective functions and an indole that is a building block of many biologically active compounds, such as a variety of neurotransmitters, are reacted in a transformation building upon Mannich bases. The reaction yields triarylmethane derivatives containing two...

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Main Authors: Bálint Lőrinczi, Péter Simon, István Szatmári
Format: Article
Language:English
Published: MDPI AG 2022-06-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:https://www.mdpi.com/1422-0067/23/13/7152
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author Bálint Lőrinczi
Péter Simon
István Szatmári
author_facet Bálint Lőrinczi
Péter Simon
István Szatmári
author_sort Bálint Lőrinczi
collection DOAJ
description KYNAs, a compound with endogenous neuroprotective functions and an indole that is a building block of many biologically active compounds, such as a variety of neurotransmitters, are reacted in a transformation building upon Mannich bases. The reaction yields triarylmethane derivatives containing two biologically potent skeletons, and it may contribute to the synthesis of new, specialised neuroprotective compounds. The synthesis has been investigated via two procedures and the results were compared to those of previous studies. A possible alternative reaction route through acid catalysis has been established.
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spelling doaj.art-643419e630b643519c0df2e9b4a0f6602023-11-23T20:08:58ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-06-012313715210.3390/ijms23137152Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich BasesBálint Lőrinczi0Péter Simon1István Szatmári2Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryInstitute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, HungaryKYNAs, a compound with endogenous neuroprotective functions and an indole that is a building block of many biologically active compounds, such as a variety of neurotransmitters, are reacted in a transformation building upon Mannich bases. The reaction yields triarylmethane derivatives containing two biologically potent skeletons, and it may contribute to the synthesis of new, specialised neuroprotective compounds. The synthesis has been investigated via two procedures and the results were compared to those of previous studies. A possible alternative reaction route through acid catalysis has been established.https://www.mdpi.com/1422-0067/23/13/7152kynurenic acidindoleMannich baseMannich reactiontriarylmethanesbioconjugates
spellingShingle Bálint Lőrinczi
Péter Simon
István Szatmári
Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
International Journal of Molecular Sciences
kynurenic acid
indole
Mannich base
Mannich reaction
triarylmethanes
bioconjugates
title Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
title_full Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
title_fullStr Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
title_full_unstemmed Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
title_short Synthesis of Indole-Coupled KYNA Derivatives via C–N Bond Cleavage of Mannich Bases
title_sort synthesis of indole coupled kyna derivatives via c n bond cleavage of mannich bases
topic kynurenic acid
indole
Mannich base
Mannich reaction
triarylmethanes
bioconjugates
url https://www.mdpi.com/1422-0067/23/13/7152
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