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

Synthesis Of Biologically Active Bis(Indolyl)Methane Derivatives by Bisindole Alkylation of... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

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

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References (80)

Publisher
Wiley
Copyright
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201600415
Publisher site
See Article on Publisher Site

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.

Journal

Asian Journal of Organic ChemistryWiley

Published: Apr 1, 2017

Keywords: ; ; ; ;

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