Synthesis of new C-3 substituted kynurenic acid derivatives

Bálint Lorinczi, Antal Csámpai, Ferenc Fülöp, István Szatmári

Research output: Contribution to journalArticle

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.

Original languageEnglish
Article number937
JournalMolecules
Volume25
Issue number4
DOIs
Publication statusPublished - Feb 19 2020

    Fingerprint

Keywords

  • DFT calculations
  • Kynurenic acid
  • Mannich reaction
  • Neuroprotective activity

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this