咪唑[1,5-a]喹啉1,4偶极环加成法合成螺[氧吲哚-3,3'-吡咯]的热力学控制。

IF 1.8 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences Pub Date : 2023-03-28 DOI:10.1515/znc-2022-0085

Areej M Jaber, Jalal A Zahra, Mustafa M El-Abadelah, Salim S Sabri, Dua'a S Sabbah

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引用次数: 1

摘要

以二甲基乙酰二羧酸酯、1-苯基咪唑[1,5- A]喹啉和n-烷基化蛋白为原料，在60℃~ 60℃的氯仿条件下，一锅反应合成了一系列新的2-(喹啉-2-基)-螺[3,3'-吡咯啉]。本文给出了观测到的热力学控制路径的合理机理。有趣的是，从5-氯-1-甲基化atin衍生的螺旋加合物对MCF7、A549和Hela人细胞系(IC50≃7 μM)表现出良好的抗增殖活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Thermodynamic control synthesis of spiro[oxindole-3,3'-pyrrolines] via 1,4-dipolar cycloaddition utilizing imidazo[1,5-a]quinoline.

A series of novel 2-(quinolin-2-yl)-spiro[oxindole-3,3'-pyrrolines] were synthesized by one-pot three-component reaction involving dimethyl acetylenedicarboxylate, 1-phenylimidazo[1,5-a]quinoline and N-alkylisatins in chloroform at ∼60 °C for 24 h. Structures of these new spiro derivatives were deduced from HRMS and NMR spectral data. A plausible mechanism for the observed thermodynamic control pathway is presented herewith. Interestingly, the spiro adduct, derived from 5-chloro-1-methylisatin, exhibited excellent antiproliferative activity on MCF7, A549 and Hela human cell lines (IC₅₀ ≃ 7 μM).

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来源期刊

Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences 生物-生化与分子生物学

CiteScore

4.10

自引率

5.00%

发文量

期刊介绍： A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal and a community resource for the emerging field of natural and natural-like products. The journal publishes original research on the isolation (including structure elucidation), bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and their biological activity and innovative developed computational methods for predicting the structure and/or function of natural products. A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) welcomes research papers in fields on the chemistry-biology boundary which address scientific ideas and approaches to generate and understand natural compounds on a molecular level and/or use them to stimulate and manipulate biological processes.