Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Natalie C Ulrich; John G Kodet; Nolan R Mente; Craig H Kuder; John A Beutler; Raymond J Hohl; David F Wiemer

doi:10.1016/j.bmc.2009.12.063

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Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

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Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure

Natalie C Ulrich, John G Kodet, Nolan R Mente, Craig H Kuder, John A Beutler, Raymond J Hohl and David F Wiemer

Bioorganic & medicinal chemistry, Vol.18(4), pp.1676-1683

02/15/2010

DOI: 10.1016/j.bmc.2009.12.063

PMCID: PMC5520629

PMID: 20116262

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Abstract

Synthesis of a set of schweinfurthin analogues varied in the D-ring alkyl substituent and stilbene moiety has been accomplished, and the activity of these compounds has been measured in a two-cell line screen. The most potent analogue and a much less active compound also were tested in the NCI 60-cell line assay, and showed comparable potency in that more extensive screen. The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute’s 60-cell line screen. An interest in determination of their cellular or molecular target has inspired our efforts to prepare both the natural products and analogues. In this paper, chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported.

Bioassay

Schweinfurthin

Anti-proliferative

Synthesis

Stilbene

Details

Title: Subtitle: Structural analogues of schweinfurthin F: Probing the steric, electronic, and hydrophobic properties of the D-ring substructure
Creators: Natalie C Ulrich - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
John G Kodet - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
Nolan R Mente - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
Craig H Kuder - Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1294, USA
John A Beutler - Molecular Targets Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD 21701, USA
Raymond J Hohl - Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1294, USA
David F Wiemer - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry, Vol.18(4), pp.1676-1683
DOI: 10.1016/j.bmc.2009.12.063
PMID: 20116262
PMCID: PMC5520629
NLM abbreviation: Bioorg Med Chem
ISSN: 0968-0896
eISSN: 1464-3391
Publisher: Elsevier Ltd
Language: English
Date published: 02/15/2010
Academic Unit: Neuroscience and Pharmacology; Chemistry; Internal Medicine
Record Identifier: 9983985931902771

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