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Synthesis of New C-3 Substituted Kynurenic Acid Derivatives

Authors
  • Lőrinczi, Bálint1, 2
  • Csámpai, Antal
  • Fülöp, Ferenc1, 2
  • Szatmári, István1, 2
  • 1 (F.F.)
  • 2 0 Szeged, Hungary
Type
Published Article
Journal
Molecules
Publisher
MDPI AG
Publication Date
Feb 19, 2020
Volume
25
Issue
4
Identifiers
DOI: 10.3390/molecules25040937
PMID: 32093108
PMCID: PMC7071119
Source
PubMed Central
Keywords
License
Green

Abstract

The application of kynurenic acid (KYNA) as an electron-rich aromatic system in the modified Mannich reaction has been examined. The extension possibility of the reaction was tested by using amines occurring in a number of bioactive products, such as morpholine, piperidine, or N -methylpiperazine and aldehydes of markedly different reactivities, like formaldehyde and benzaldehyde. The influence of substituents attached to position 3 on the aminoalkylation was also investigated. Thus, reactions of 3-carbamoyl-substituted precursors with tertiary amine containing side-chains were also tested to afford new KYNA derivatives with two potential cationic centers. By means of NMR spectroscopic measurements, supported by DFT calculations, the dominant tautomer form of KYNA derivatives was also determined.

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