Bronsted Acid Catalyzed Bisindolization of -Amido Acetals: Synthesis and Anticancer Activity of Bis(indolyl)ethanamino Derivatives

被引：33

作者：

Mari, Michele ^{[1
]}

Tassoni, Aurora ^{[2
]}

Lucarini, Simone ^{[1
]}

Fanelli, Mirco ^{[2
]}

Piersanti, Giovanni ^{[1
]}

Spadoni, Gilberto ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Dept Biomol Sci, I-61029 Urbino, PU, Italy

[2] Univ Urbino Carlo Bo, Dept Biomol Sci, I-61032 Fano, PU, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 18期

关键词：

Medicinal chemistry; Drug discovery; Antitumor agents; Cytotoxicity; Natural products; Alkaloids; Nitrogen heterocycles; IN-VITRO; INDOLE ALKALOIDS; EFFICIENT SYNTHESIS; DRUG LEADS; 3,3'-DIINDOLYLMETHANE; INDOLE-3-CARBINOL; 3-(2'-NITROVINYL)INDOLE; ALKYLATION; ACTIVATION; PATHWAYS;

D O I：

10.1002/ejoc.201402055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A BrOnsted acid catalyzed bisindolization reaction with suitable -amido acetals that tolerates a wide range of indoles is reported. The method allows rapid access to the biologically relevant bisindolyl ethanamine scaffold in good to excellent yields upon mild amide basic hydrolysis. In preliminary pharmacological studies, some of these compounds display cytotoxic activity in U937 cancer cells. The marine natural alkaloid 2,2-di(6-bromo-3-indolyl)-ethylamine was the most active compound and could be a lead candidate for further optimization. For the first time, the biological role of this brominated bisindole marine alkaloid is presented.

引用

页码：3822 / 3830

页数：9

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