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-醌甲基化物驱动的犬尿氨酸内酰胺的合成。

-quinone methide driven synthesis of kynurenic acid lactams.

作者信息

Sárik Julián Robin, Hetényi Anasztázia, Berkecz Róbert, Szatmári István, Lőrinczi Bálint

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged Eötvös u. 6 H-6720 Szeged Hungary

Department of Medical Chemistry, University of Szeged Dóm tér 8 H-6720 Szeged Hungary.

出版信息

RSC Adv. 2024 Jul 12;14(31):22123-22131. doi: 10.1039/d4ra04341c.

DOI:10.1039/d4ra04341c
PMID:39005244
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11240218/
Abstract

Lactam formation of different KYNA amides and Mannich bases mediated by -quinone methide has been investigated. The efficiency of the two routes of the cyclization process was revealed and the influence of diverse amide side chains was explored. In this regard compounds bearing a tertiary amine function in the amide side chain resulted in the formation of the lactam product, while the formation of dimer derivatives was observed in the case of other KYNA amides. Furthermore, derivatives bearing different substituents on the KYNA B ring were synthesized and their effects on the ring-closure reaction were investigated.

摘要

研究了由醌甲基化物介导的不同犬尿喹啉酸酰胺和曼尼希碱的内酰胺形成。揭示了环化过程两条路线的效率,并探索了不同酰胺侧链的影响。在这方面,酰胺侧链带有叔胺官能团的化合物导致内酰胺产物的形成,而在其他犬尿喹啉酸酰胺的情况下观察到二聚体衍生物的形成。此外,合成了在犬尿喹啉酸B环上带有不同取代基的衍生物,并研究了它们对闭环反应的影响。

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本文引用的文献

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Synthesis of Indole-Coupled KYNA Derivatives via C-N Bond Cleavage of Mannich Bases.通过曼尼希碱的 C-N 键断裂合成吲哚偶联的 KYNA 衍生物。
Int J Mol Sci. 2022 Jun 28;23(13):7152. doi: 10.3390/ijms23137152.
2
Synthetic- and DFT modelling studies on regioselective modified Mannich reactions of hydroxy-KYNA derivatives.羟基犬尿喹啉酸衍生物区域选择性修饰曼尼希反应的合成及密度泛函理论建模研究
RSC Adv. 2020 Dec 24;11(1):543-554. doi: 10.1039/d0ra08325a. eCollection 2020 Dec 21.
3
Synthesis of New C-3 Substituted Kynurenic Acid Derivatives.
新型 C-3 取代色氨酸酸衍生物的合成。
Molecules. 2020 Feb 19;25(4):937. doi: 10.3390/molecules25040937.
4
Structural Evaluation and Electrophysiological Effects of Some Kynurenic Acid Analogs.一些犬尿氨酸类似物的结构评估和电生理效应。
Molecules. 2019 Sep 26;24(19):3502. doi: 10.3390/molecules24193502.
5
Mannich base-connected syntheses mediated by -quinone methides.由对醌甲基化物介导的曼尼希碱连接的合成反应。
Beilstein J Org Chem. 2018 Mar 6;14:560-575. doi: 10.3762/bjoc.14.43. eCollection 2018.
6
Study of 2-aminoquinolin-4(1H)-one under Mannich and retro-Mannich reaction.2-氨基喹啉-4(1H)-酮在曼尼希反应和逆曼尼希反应条件下的研究
PLoS One. 2017 May 30;12(5):e0175364. doi: 10.1371/journal.pone.0175364. eCollection 2017.
7
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Cephalalgia. 2017 Nov;37(13):1272-1284. doi: 10.1177/0333102416678000. Epub 2016 Nov 16.
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Med Res Rev. 2015 Jul;35(4):753-89. doi: 10.1002/med.21342. Epub 2015 Mar 21.
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