Synthesis Of Biologically Active Bis(Indolyl)Methane Derivatives by Bisindole Alkylation of Tetrahydroisoquinolines with Visible-Light Induced Ring-Opening Fragmentation

被引：26

作者：

Chen, Chia-Chueng ^{[1
]}

Hong, Bor-Cherng ^{[1
]}

Li, Wen-Shan ^{[2
]}

Chang, Tzu-Ting ^{[2
]}

Lee, Gene-Hsiang ^{[3
]}

机构：

[1] Natl Chung Cheng Univ, Dept Chem & Biochem, 168 Univ Rd, Chiayi 621, Taiwan

[2] Acad Sinica, Inst Chem, 128,Sec 2,Acad Rd, Taipei 115, Taiwan

[3] Natl Taiwan Univ, Instrumentat Ctr, 1,Sec 4,Roosevelt Rd, Taipei 106, Taiwan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 04期

关键词：

anticancer; bisindole; catalysis; fragmentation; photoredox; C-C BOND; N-ARYL-TETRAHYDROISOQUINOLINES; PHOTOREDOX CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; ANTIMICROBIAL ACTIVITY; COUPLING REACTION; DUAL CATALYSIS; INDOLES; EFFICIENT; CLEAVAGE;

D O I：

10.1002/ajoc.201600415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light photoredox catalyzed ring-opening functionalization of tetrahydroisoquinolines with bisindole alkylation has been developed, which expedites a new vista for the synthesis of bis(indolyl)methane derivatives. The transformation comprises a series of cascade reactions, photoredox catalysis, amine oxidation, fragmentation and Friedel-Craft alkylation. Five of the prepared bis(indolyl)methane derivatives containing the para substitution group on the side chain of benzene suppressed cancer cell growth in human breast adenocarcinoma MDA-MB-231 cells, and one candidate demonstrated a significant effect on cell migration.

引用

页码：426 / 431

页数：6

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