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Synthesis and structure revision of tyroscherin, and bioactivities of its stereoisomers against IGF-1-dependent tumor cells |
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| Authors: | Ken Ishigami Chié Shibata Hidenori Watanabe Takeshi Kitahara |
| Institution: | a Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan b Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan c School of Pharmacy, Teikyo Heisei University, 2289 Uruido, Ichihara City, Chiba 290-0193, Japan |
| Abstract: | Synthesis of the proposed structure of tyroscherin, a growth inhibitor of IGF-1-dependent cancer cells, was succeeded by one-pot Julia coupling. However, spectral data of the synthetic compound were not identical with those of natural tyroscherin. The stereochemistry of tyroscherin is revised to be 2S,3R,8R,10R by syntheses of stereoisomers. Synthetic tyroscherin showed more potent activity than its stereoisomers against IGF-1-dependent cancer cells. |
| Keywords: | Tyroscherin Inhibitor of IGF-1-dependent cell growth Structure revision One-pot Julia coupling |
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