Abstract
Total syntheses of (+)-dictyoceratin-C (1) and (+)-dictyoceratin-A (smenospondiol) (2), hypoxia-selective growth inhibitors isolated from marine sponge, were executed. The absolute stereochemistry of the each compound was determined through the enantioselective total syntheses of them. It revealed that the unnatural enantiomers of them also exhibited the hypoxia-selective growth inhibitory activity against human prostate cancer DU-145 cells.
Keywords:
(+)-Dictyoceratin-A (smenospondiol); (+)-Dictyoceratin-C; Absolute stereochemistry; Hypoxia-selective growth inhibitor; Total synthesis.
Copyright © 2015 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Cell Hypoxia
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Cell Line, Tumor
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Cell Proliferation / drug effects*
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Drug Screening Assays, Antitumor
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Growth Inhibitors / chemical synthesis*
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Growth Inhibitors / chemistry
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Growth Inhibitors / pharmacology*
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Humans
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Hydroxybenzoates / chemical synthesis*
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Hydroxybenzoates / chemistry
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Hydroxybenzoates / pharmacology*
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Male
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Marine Biology
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Porifera / chemistry*
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Prostatic Neoplasms / pathology
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Sesquiterpenes / chemical synthesis*
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Sesquiterpenes / chemistry
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Sesquiterpenes / pharmacology*
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Stereoisomerism
Substances
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Growth Inhibitors
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Hydroxybenzoates
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Sesquiterpenes
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dictyoceratin-C
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smenospondiol