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Paper | Special issue | Vol 86, No. 1, 2012, pp.281-303
Published online, 2nd May, 2012
DOI: 10.3987/COM-12-S(N)8
Synthesis of Antineoplastic Analogs of Aplysiatoxin with Various Side Chain Structures

Yuki Shu, Ryo C. Yanagita, Harukuni Tokuda, Nobutaka Suzuki, and Kazuhiro Irie*

*Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kitashirakawa Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan

Abstract

We have recently developed a simplified analog of aplysiatoxin with anti-proliferative activity (1). To investigate the structure–activity relationship of its side chain, an alternative synthetic route of 1 has been established. Via the key intermediate 6, p-hydroxyl or o,m-dihydroxyl derivatives (4 and 5) as well as 1 were synthesized and their biological activities were evaluated. Although the position of the hydroxyl group in the benzene ring did not change the affinity for protein kinase C isozymes or the ability to induce the Epstein-Barr virus early antigen, anti-proliferative activities against several human cancer cell lines of 1 were superior to those of 4.