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通过一步多组分合成可获得的吡喃并[3,2-c]吡啶酮的抗增殖和诱导凋亡特性。

Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis.

作者信息

Magedov Igor V, Manpadi Madhuri, Evdokimov Nikolai M, Elias Eerik M, Rozhkova Elena, Ogasawara Marcia A, Bettale Jennifer D, Przheval'skii Nikolai M, Rogelj Snezna, Kornienko Alexander

机构信息

Department of Organic Chemistry, Timiryazev Agriculture Academy, Moscow 127550, Russia.

出版信息

Bioorg Med Chem Lett. 2007 Jul 15;17(14):3872-6. doi: 10.1016/j.bmcl.2007.05.004. Epub 2007 May 6.

DOI:10.1016/j.bmcl.2007.05.004
PMID:17512729
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3383048/
Abstract

4-Arylpyrano-[3,2-c]-pyridones have been prepared by a one-step cyclocondensation of 4-hydroxy-1,6-dimethylpyridin-2(1H)-one with various substituted benzaldehydes and malononitrile. These heterocycles exhibit micromolar and submicromolar antiproliferative activity in HeLa and induce apoptosis in Jurkat cell lines. Structure-activity studies performed on a small library of these compounds show a pronounced cytotoxicity enhancing effect of the bromo substituent at the meta position of the C4 aromatic moiety.

摘要

通过4-羟基-1,6-二甲基吡啶-2(1H)-酮与各种取代苯甲醛和丙二腈的一步环缩合反应制备了4-芳基吡喃并-[3,2-c]-吡啶酮。这些杂环化合物在HeLa细胞中表现出微摩尔和亚微摩尔级别的抗增殖活性，并在Jurkat细胞系中诱导细胞凋亡。对这些化合物的一个小文库进行的构效关系研究表明，C4芳基部分间位的溴取代基具有显著的细胞毒性增强作用。