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Paper | Regular issue | Vol 92, No. 4, 2016, pp.664-679
Published online, 10th February, 2016
DOI: 10.3987/COM-16-13404
Synthesis and in vitro Antitumor Activity of 9-Hydroxyellipticine Derivatives with Glucose Conjugation via Triazolylmethyl Succinate Linker

Naoya Sato, Yu Kawai, Yosuke Akaba, Shoji Honma, Norio Sakai, and Takeo Konakahara*

*Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


Three types of novel 9-hydroxyellipticine derivatives 7a-c with glucose conjugation, linked by a triazolylmethyl succinic ester bond, were synthesized, and their cytotoxicity against HeLa S-3 and 293T cells was evaluated together with ellipticine (1) and 9-hydroxyellipticine (3). These new compounds 7a-c exhibited potent antitumor activity against HeLa S-3 and 293T, and water solubility of 7a was greatly higher than those of 1 and 3. The effects of an -OCH2CH2- spacer and the amino sugar moiety on the antitumor activity were examined using 7b,c. Furthermore, one of these glucose-conjugates 7a was applied to hydrolysis, catalyzed by carboxyesterase, leading to the formation of 3 under physiological conditions.