- 著者
-
Kita Masaki
Oka Hirotaka
Usui Akihiro
Ishitsuka Tomoya
Mogi Yuzo
Watanabe Hidekazu
- 出版者
- Elsevier
- 雑誌
- Tetrahedron (ISSN:00404020)
- 巻号頁・発行日
- vol.68, no.42, pp.8753-8760, 2012-10
- 被引用文献数
-
7
Mycalolides are tris-oxazole macrolides isolated from the marine sponge Mycale sp., which shows cytotoxic, antifungal, and actin-depolymerizing activities. To develop an efficient synthetic route of mycalolides and to evaluate its functional mechanism of biological activities, tris-oxazole macrolactone analogs of mycalolides were synthesized through the use of ring-closing metathesis (RCM). The presence/absence of protecting groups at C3, solvent polarity, and reaction temperature significantly affected the stereoselectivity of RCM (E/Z=2.5/1.0–1.0/2.5). The 19E- and 19Z-stereoisomers both exhibited moderate cytotoxicity against tumor cells, but neither showed significant actin-depolymerizing properties or antimycotic activity against pathogenic fungi. Thus, both the side-chain (actin-binding) moiety and the macrolactone moiety were suggested to be essential for the potent biological activities of the parent molecules.