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Synthesis of amide isosteres of schweinfurthin-based stilbenes

  1. Author:
    Stockdale, David P
    Beutler, John
    Wiemer, David F

  2. Author Address

    Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, United States., Molecular Targets Laboratory, Center for Cancer Research, NCI-Frederick, Frederick, MD 21702, United States., Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, United States. Electronic address: david-wiemer@uiowa.edu.,
    1. Year: 2017
    2. Date: Oct 15
    3. Epub Date: 2017 Aug 09
  2. Journal: Bioorganic & medicinal chemistry
    1. 25
    2. 20
    3. Pages: 5483-5489
  4. Type of Article: Article
  5. ISSN: 0968-0896
  1. Abstract:

    The schweinfurthins are plant-derived stilbenes with an intriguing profile of anti-cancer activity. To obtain analogues of the schweinfurthins that might preserve the biological activity but have greater water solubility, a formal replacement of the central olefin with an amide has been explored. Two pairs of amides have been prepared, each containing the same hexahydroxanthene "left half" joined through an amide linkage to two different "right halves." In each series, the amide has been inserted in both possible orientations, placing the carbonyl group on the tricyclic ABC ring system and the amine on the D-ring, or placing the amine on the hexahydroxanthene and the carbonyl group on the D-ring. The four new schweinfurthin analogues have been tested in the NCI 60 cell line screen, and in both cases the more active isomer carried the carbonyl group on the C-ring. Copyright © 2017. Published by Elsevier Ltd.

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External Sources

  1. View Full Text
  2. DOI: 10.1016/j.bmc.2017.08.016
  3. PMID: 28866376
  4. View record in Web of Science®
  5. WOS: 000413402100030

Library Notes

  1. Fiscal Year: FY2016-2017
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