期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 9, 期 7, 页码 1922-1932出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201402202
关键词
asymmetric synthesis; ion channels; natural products; structure-activity relationships; total synthesis
资金
- MEXT
- Daiichi Sankyo Foundation of Life Science
- Yamada Science Foundation
- Suntory Institute for Bioorganic Research
- Grants-in-Aid for Scientific Research [24580161, 23102015, 26292057, 26660094] Funding Source: KAKEN
Tetrodotoxin, a toxic principle of puffer fish intoxication, is one of the most famous marine natural products owing to its complex structure and potent biological activity, which leads to fatal poisoning. Continuous synthetic studies on tetrodotoxin and its analogues to elucidate biologically interesting issues associated with tetrodotoxin have led to the development of versatile routes for a variety of tetrodotoxin derivatives. With the aim of investigating the structure-activity relationship of tetrodotoxin with voltage-gated sodium channels, this study describes the first total syntheses of 5-de-oxytetrodotoxin, a natural analogue of tetrodotoxin, and 8-deoxytetrodotoxin, an unnatural analogue, from a newly designed, versatile intermediate in an efficient manner. An estimation of the biological activities of these compounds reveals the importance of the hydroxy groups at the C-5 and C-8 positions on the inhibition of voltage-gated sodium channels.
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