Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity.

Abstract

Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expanding the size of its F ring and determined their effects on the proliferation of cancer cell lines. All changes to the F-ring of hippuristanol resulted in 3-fold to >100-fold decrease in activity.

• Authors: Wei Li, Yongjun Dang, Jun O Liu, Biao Yu
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 20 Issue 10 Pg. 3112-5 (May 15 2010) ISSN: 1464-3405 [Electronic] England
• PMID: 20409710 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright 2010 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Furans
• Spiro Compounds
• Sterols
• hippuristanol
• spiroketal

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Furans (chemistry)
• HeLa Cells
• Humans
• Spiro Compounds (chemistry)
• Stereoisomerism
• Sterols (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship