A simple BF3 Et2O-mediated cycloaddition reaction to the formation of cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids

Tan, Siow-Ping

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Type :	article
Subject :	Q Science (General)
ISSN :	1570-1786
Main Author :	Tan, Siow-Ping
Additional Authors :	Nafiah Mohd Azlan
Title :	A simple BF3 Et2O-mediated cycloaddition reaction to the formation of cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids

Place of Production :	Tanjung Malim
Publisher :	Fakulti Sains dan Matematik
Year of Publication :	2021
Notes :	Letters in Organic Chemistry
Corporate Name :	Universiti Pendidikan Sultan Idris
HTTP Link :	Click to view web link

Abstract : Universiti Pendidikan Sultan Idris

A Lewis acid BF3?Et2O-mediated intramolecular cycloaddition reaction of mahanimbine (1) is described. Three cycloadducts, bicyclomahanimbine (2), cyclomahanimbine (3) and murrayazolinine (4) were obtained. The structural characterization of these compounds was determined by 1D and 2D NMR experiments. These compounds showed no cytotoxic activity against human MRC-5 cells (IC50 > 60 ?g/mL). Compound 3 showed the highest inhibition cytotoxic effects against HeLa and HL-60 cancer cells with IC50 values of 10.0 and 28.7 ?g/mL, respectively. This strategy opens a new approach for the synthesis of biologically significant cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids. ? 2021 Bentham Science Publishers.

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