Preparation of Naphthoquinone Derivatives from Plumbagin and Their Ichthyotoxicity.

K Ogihara, R Yamashiro, M Higa, S YOGI

Index: Ogihara, Kazuhito; Yamashiro, Rieko; Higa, Matsutake; Yogi, Seiichi Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 3 p. 437 - 445

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Citation Number: 11

Abstract

Various naphthoquinone derivatives were prepared from a natural product, 5-hydroxy-2- methyl-1, 4-naphthoquinone (plumbagin); these were mostly substituted at C-3 through carbon-carbon bond formation mediated by a metal-based oxidant such as lead tetraacetate in the presence of various carboxylic acids. The halogenated compounds showed stronger ichthyotoxicity than plumbagin, but other derivatives were less active.