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

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Title
A simple BF3 Et2O-mediated cycloaddition reaction to the formation of cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids
Type
Article
Main Author
Tan, Siow-Ping
Additional Authors
  • Nafiah Mohd Azlan
Subject
Q Science (General)
ISSN
1570-1786
Language Code
eng
Bibliographic Details
Place of Production
Tanjung Malim
Publisher
Fakulti Sains dan Matematik
Year of publication
2021
Notes
Letters in Organic Chemistry
Degree Type
Others
Corporate Name
Universiti Pendidikan Sultan Idris

Abstract

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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