Relevance of the C-5 position to schweinfurthin induced cytotoxicity

Joseph J Topczewski; Michael P Callahan; John G Kodet; Jery D Inbarasu; Nolan R Mente; John A Beutler; David F Wiemer

doi:10.1016/j.bmc.2011.10.034

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Relevance of the C-5 position to schweinfurthin induced cytotoxicity

Journal article

Peer reviewed

Relevance of the C-5 position to schweinfurthin induced cytotoxicity

Joseph J Topczewski, Michael P Callahan, John G Kodet, Jery D Inbarasu, Nolan R Mente, John A Beutler and David F Wiemer

Bioorganic & medicinal chemistry, Vol.19(24), pp.7570-7581

12/15/2011

DOI: 10.1016/j.bmc.2011.10.034

PMCID: PMC3232010

PMID: 22055715

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Abstract

The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay.

Apoptosis

Bioassay

Anti-proliferative

Cytotoxic

Schweinfurthins

Details

Title: Subtitle: Relevance of the C-5 position to schweinfurthin induced cytotoxicity
Creators: Joseph J Topczewski - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
Michael P Callahan - 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
Jery D Inbarasu - 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
John A Beutler - Molecular Targets Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, 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.19(24), pp.7570-7581
DOI: 10.1016/j.bmc.2011.10.034
PMID: 22055715
PMCID: PMC3232010
NLM abbreviation: Bioorg Med Chem
ISSN: 0968-0896
eISSN: 1464-3391
Publisher: Elsevier Ltd
Language: English
Date published: 12/15/2011
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985844302771

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