| Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside. | |
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MedLine Citation:
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PMID: 23015368 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Hayato Fukuda; Yuko Nishiyama; Shiina Nakamura; Yutaro Ohno; Tadashi Eguchi; Yoshiharu Iwabuchi; Takeo Usui; Naoki Kanoh |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-9-27 |
Journal Detail:
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Title: Chemistry, an Asian journal Volume: - ISSN: 1861-471X ISO Abbreviation: Chem Asian J Publication Date: 2012 Sep |
Date Detail:
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Created Date: 2012-9-27 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101294643 Medline TA: Chem Asian J Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Affiliation:
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Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-9578 (Japan), Fax: (+81) 22-795-6847. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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