ArticleRSC advances2020
Synthetic- and DFT modelling studies on regioselective modified Mannich reactions of hydroxy-KYNA derivatives.
Article in RSC advances, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Taming unconventional nucleic acid structures: synthesis of acridine- and 1,10-phenanthroline-based G-quadruplex binders.RSC advances · 2026Review
- Synthesis and Transformation of Tricyclic KYNA Derivatives.International journal of molecular sciences · 2025Article
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- Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1Molecules (Basel, Switzerland) · 2023Article
- Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters.ACS omega · 2023Article
- Synthesis of 4-Hydroxyquinolines as Potential Cytotoxic Agents.International journal of molecular sciences · 2022Article
- Synthesis of Indole-Coupled KYNA Derivatives via C-N Bond Cleavage of Mannich Bases.International journal of molecular sciences · 2022Article
- Synthesis of quinolinesRSC advances · 2021Article
- KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect.International journal of molecular sciences · 2021Review
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4 authors.
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Abstract
The syntheses of hydroxy-substituted kynurenic acid (KYNA) derivatives have been achieved by an optimised Conrad-Limpach procedure. The derivatives were then reacted with morpholine and paraformaldehyde, as a representative amine and aldehyde, in a modified Mannich reaction. The newly introduced substituents altered the preferred reaction centre of the KYNA skeleton. A systematic investigation of substitutions was carried out, using different reaction conditions, resulting in mono- or disubstituted derivatives. Product selectivity and regioselectivity were rationalised by DFT calculations disclosing HOMO distribution and NBO charges on the potential nucleophilic centres in the anion of the appropriate KYNA ester assumed to be active components towards the iminium ion intermediate.
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