Enantioselective synthesis of dictyoceratin-A (smenospondiol) and -C, hypoxia-selective growth inhibitors from marine sponge.

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.

• Authors: Yuji Sumii, Naoyuki Kotoku, Akinori Fukuda, Takashi Kawachi, Yuta Sumii, Masayoshi Arai, Motomasa Kobayashi
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 23 Issue 5 Pg. 966-75 (Mar 01 2015) ISSN: 1464-3391 [Electronic] England
• PMID: 25659617 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2015 Elsevier Ltd. All rights reserved.

Chemical References

• Growth Inhibitors
• Hydroxybenzoates
• Sesquiterpenes
• dictyoceratin-C
• smenospondiol

Topics

• Animals
• Cell Hypoxia
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Drug Screening Assays, Antitumor
• Growth Inhibitors (chemical synthesis, chemistry, pharmacology)
• Humans
• Hydroxybenzoates (chemical synthesis, chemistry, pharmacology)
• Male
• Marine Biology
• Porifera (chemistry)
• Prostatic Neoplasms (pathology)
• Sesquiterpenes (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism