Synthesis Of Biologically Active Bis(Indolyl)Methane Derivatives by Bisindole Alkylation of Tetrahydroisoquinolines with Visible‐Light Induced Ring‐Opening Fragmentation. Issue 4 (13th October 2016)

• Record Type: Journal Article
• Authors: Chen, Chia‐Chueng; Hong, Bor‐Cherng; Li, Wen‐Shan; Chang, Tzu‐Ting; Lee, Gene‐Hsiang
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 4(2017)
• Page Start: 426
• Page End: 431
• Publication Date: 2016-10-13
• Subjects: anticancer -- bisindole -- catalysis -- fragmentation -- photoredox; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600415
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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. Abstract : A visible‐light photoredox catalyzed ring‐opening functionalization of tetrahydroisoquinolines with bisindole alkylation has been developed and applied to synthesize biologically active bis(indolyl)methane derivatives that suppress cancer cell growth in human breast adenocarcinoma MDA‐MB‐231 cells, one of which has an important influence on cell migration.