Av isible-light photoredoxc atalyzed ring-opening functionalization of tetrahydroisoquinolines with bisindole alkylation has been developed, which expedites an ew vista for the synthesis of bis(indolyl)methaned erivatives. The transformation comprises as eries 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 asignificant effect on cell migration.Bis(indolyl)m ethanes (BIMs), [1] are an importantt ype of alkaloid that have been widely isolated from marine and terrestrial natural sources, including plants, parasitic bacteria, tunicates, and sponges, etc. (Figure 1). [2] This BIMs alkaloids exhibit ab road spectrum of biological activities including antibacterial, [3] antitumor, [4] antimicrobial, [5] anti-fungal, [6] anti-inflammatory, [7] anti-hyperlipidemic, [8] antimetastatic, [9] and serve as poten-tial hypolipidemic and antiobesity agents, [10] etc. Moreover,t he oxidizedf orms of BIMs are utilized as colorimetric sensors. [11] Owing to their versatile activity and their prevalence in natural resources, syntheses of BIMs have continued to be of intense interest. While the condensation of indoles and carbonyl compounds in the presence of either protic acid or Lewis acid is the most traditional and practical methodf or the synthesis of bis(indolyl)methanes, [12] diversea pproaches toward BIMs have continued to thrive (Scheme1). Their importance can be Scheme1.Selectedexamples of the approaches to BIMs.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.