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■ Synthesis, Photochemical Properties, and Cytotoxicity of 10-Alkylphenazin-2(10H)-ones

Haruki Kohatsu, Shogo Kamo, Takuya Hosokai, Shinji Kamisuki, Yutaro Machida, Ryota Kobayashi, Tsuneomi Kawasaki, Kenji Ohgane, and Kouji Kuramochi*

*Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

In the present study, the synthesis of a variety of 10-alkylphenazin-2(10H)-ones by oxidative coupling between N-alkylbenzene-1,2-diamine and 1,2,4-benzenetriol under an oxygen atmosphere was realized, and their photochemical and biological properties were investigated. 10-Methylphenazin-2(10H)-one, a reddish orange pigment, exhibited fluorescence in the visible light region upon exposure to ultraviolet light. Interestingly, the fluorescence from 10-methylphenazin-2(10H)-one consisted of two components. In addition, the cytotoxic evaluation of various synthetic compounds was performed. Among the compounds tested in this study, 10-methylphenazin-2(10H)-one exhibited the most selective cytotoxic activity against human cancer A549 cells compared to normal MRC-5 cells.