Synthesis of amide isosteres of schweinfurthin-based stilbenes

David P Stockdale; John A Beutler; David F Wiemer

doi:10.1016/j.bmc.2017.08.016

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Synthesis of amide isosteres of schweinfurthin-based stilbenes

Journal article

Peer reviewed

Synthesis of amide isosteres of schweinfurthin-based stilbenes

David P Stockdale, John A Beutler and David F Wiemer

Bioorganic & medicinal chemistry, Vol.25(20), pp.5483-5489

10/15/2017

DOI: 10.1016/j.bmc.2017.08.016

PMCID: PMC5763908

PMID: 28866376

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https://www.ncbi.nlm.nih.gov/pmc/articles/5763908View

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Abstract

[Display omitted] 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.

Schweinfurthin

Amide isostere

Stilbene

Cancer

Details

Title: Subtitle: Synthesis of amide isosteres of schweinfurthin-based stilbenes
Creators: David P Stockdale - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, United States
John A Beutler - Molecular Targets Laboratory, Center for Cancer Research, NCI-Frederick, Frederick, MD 21702, United States
David F Wiemer - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, United States
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry, Vol.25(20), pp.5483-5489
DOI: 10.1016/j.bmc.2017.08.016
PMID: 28866376
PMCID: PMC5763908
NLM abbreviation: Bioorg Med Chem
ISSN: 0968-0896
eISSN: 1464-3391
Publisher: Elsevier Ltd
Grant note: DOI: 10.13039/100001024, name: Roy J. Carver Charitable Trust
Language: English
Date published: 10/15/2017
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985830502771

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