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Paper | Special issue | Vol 70, No. 1, 2006, pp.491-499
Published online, 24th October, 2006
DOI: 10.3987/COM-06-S(W)48
Synthesis of 6-Methylindole-4,7-quinone and Anti-tumor Activities of Its Related Indolequinones

Junko Nobuhiro, Miho Hirayama, Tominari Choshi, Keiichi Kamoshita, Sakiko Maruyama, Yoshikazu Sukenaga, Takashi Ishizu, Haruto Fujioka, and Satoshi Hibino*

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

We synthesized 6-methylindole-4,5-quinone (1b) in order to clarify the structure of natural product, 5-methylindole-4,5-quinone (1a) isolated from Drupella fragum. The synthesis features the construction of the indole ring based on an electrocyclic reaction of a 3-alkenyl-2-propargylpyrrole intermediate.
Two synthetic methylindolequinones and their related compounds were examined in human lung cancer cell line NCI-H460 and human breast cancer cell line MDA-MB-231.