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构建具有六氢芴并[9,1-bc]呋喃骨架手性化合物的捷径:合成与细胞毒性活性

The short way to chiral compounds with hexahydrofluoreno[9,1-bc]furan framework: synthesis and cytotoxic activity.

作者信息

Kurbakova Svetlana Yu, Il'ina Irina V, Mikhalchenko Oksana S, Pokrovsky Mikhail A, Korchagina Dina V, Volcho Konstantin P, Pokrovsky Andrey G, Salakhutdinov Nariman F

机构信息

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation.

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue, 9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation.

出版信息

Bioorg Med Chem. 2015 Apr 1;23(7):1472-80. doi: 10.1016/j.bmc.2015.02.013. Epub 2015 Feb 16.

DOI:10.1016/j.bmc.2015.02.013
PMID:25737086
Abstract

A simple and efficient method for synthesizing chiral heterocyclic compounds with the hexahydrofluoreno[9,1-bc]furan framework via interaction between trans-4-hydroxymethyl-2-carene and aromatic aldehydes containing methoxy and hydroxyl moieties in the presence of montmorillonite clay was found. One of the synthesized compounds exhibited a high cytotoxic activity against lymphoblastoid cell line MT-4 (CTD50 0.9μM), which was higher than that of the comparative drug Doxorubicin. Death of cancer cells in this case substantially occurs via induction of apoptosis.

摘要

发现了一种简单有效的方法,可通过反式-4-羟甲基-2-蒈烯与含有甲氧基和羟基部分的芳香醛在蒙脱石粘土存在下相互作用,合成具有六氢芴并[9,1-bc]呋喃骨架的手性杂环化合物。其中一种合成化合物对淋巴母细胞样细胞系MT-4表现出高细胞毒性活性(CTD50为0.9μM),高于对照药物阿霉素。在这种情况下,癌细胞的死亡主要通过诱导凋亡发生。

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