NDLI: Synthesis and structure-activity relationship of vicenistatin, a cytotoxic 20-membered macrolactam glycoside.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Fukuda, Hayato Nishiyama, Yuko Nakamura, Shiina Ohno, Yutaro Eguchi, Tadashi Iwabuchi, Yoshiharu Usui, Takeo Kanoh, Naoki
Description	Country affiliation: Japan Author Affiliation: Fukuda H ( Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-9578, Japan.)
Abstract	We have developed two syntheses of vicenistatin and its analogues. Our first-generation strategy included the rapid and sequential assembly of the macrocyclic lactam by using an intermolecular Horner-Wadsworth-Emmons reaction between the C3-C13 fragment and the C1-C2, C14-C19 fragment, followed by an intramolecular Stille coupling reaction. The second-generation strategy utilized a ring-closing metathesis of a hexaene intermediate to generate the desired 20-membered macrolactam. This second-generation strategy made it possible to prepare synthetic analogues of vicenistatin, including the C20- and/or C23-demethyl analogues. Evaluation of the cytotoxic effect of these analogues indicated the importance of the fixed conformation of aglycon for determining the biological activity of the vicenistatins.
File Format	HTM / HTML
ISSN	18614728
Issue Number	12
Volume Number	7
e-ISSN	1861471X
Journal	Chemistry - An Asian Journal
Language	English
Publisher	Wiley-VCH
Publisher Date	2012-12-01
Publisher Place	Germany
Access Restriction	Subscribed
Subject Keyword	Cell Line Research Support, Non-u.s. Gov't Macrolides Cell Survival Humans Drug Therapy Antineoplastic Agents Rats Aminoglycosides Lactams Chemical Synthesis Pharmacology Structure-activity Relationship Drug Effects Neoplasms Journal Article Chemistry Animals Glycosides Cell Line, Tumor Discipline Chemistry
Content Type	Text
Resource Type	Article
Subject Domain (in MeSH)	Cells Eukaryota Neoplasms Organic Chemicals Carbohydrates Chemical Actions and Uses Chemical Phenomena Cell Physiological Phenomena
Subject	Organic Chemistry Biochemistry

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