Synthesis and preliminary biological study of bisindolylmethanes accessed by an acid-catalyzed hydroarylation of vinyl indoles

被引：80
作者：
Pathak, Tejas P. [1 ]
Osiak, Jaroslaw G. [1 ]
Vaden, Rachel M. [1 ]
Welm, Bryan E. [2 ]
Sigman, Matthew S. [1 ]
机构：
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
[2] Huntsman Canc Inst, Dept Surg, Salt Lake City, UT 84112 USA
来源：
TETRAHEDRON | 2012年 / 68卷 / 26期
基金：
美国国家卫生研究院;
关键词：
Acid catalysis; Bisindolylmethanes; Hydroarylation; Heterocycles; Breast cancer; BREAST-CANCER CELLS; UNSYMMETRICAL BISINDOLES; 3,3'-DIINDOLYLMETHANE; INDOLE-3-CARBINOL; HYDROAMINATION; RECEPTOR;
D O I：
10.1016/j.tet.2012.03.075
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An acid-catalyzed hydroarylation reaction of vinyl indoles is reported, which tolerates a wide range of heterocycles as the exogenous nucleophile, such as indoles, pyrroles, and indolizines. The method rapidly accesses the biologically relevant bisindolylmethane scaffold in good to excellent yields. Evaluation of the biological activity of several synthesized analogues reveals cytotoxic activity against and selectivity for the MCF-7 breast cancer cell line. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5203 / 5208
页数：6
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