Document Detail

The synthesis and evaluation of flavone and isoflavone chimeras of novobiocin and derrubone.
MedLine Citation:
PMID:  19932969     Owner:  NLM     Status:  MEDLINE    
The natural products novobiocin and derrubone have both demonstrated Hsp90 inhibition and structure-activity relationships have been established for each scaffold. Given these compounds share several key structural features, we hypothesized that incorporation of elements from each could provide insight to structural features important for Hsp90 inhibition. Thus, chimeric analogues of novobiocin and derrubone were constructed and evaluated. These studies confirmed that the functionality present at the 3-position of the isoflavone plays a critical role in determining Hsp90 inhibition and suggests that the bicyclic ring system present in both novobiocin and derrubone do not share similar modes of binding.
Jared R Mays; Stephanie A Hill; Justin T Moyers; Brian S J Blagg
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2009-10-31
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  18     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2010-02-03     Completed Date:  2010-04-27     Revised Date:  2013-05-31    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  249-66     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2009 Elsevier Ltd. All rights reserved.
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Malott 4070, The University of Kansas, Lawrence, KS 66045-7563, United States.
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MeSH Terms
Antineoplastic Agents / chemical synthesis,  chemistry*,  pharmacology*
Breast Neoplasms / drug therapy
Cell Line, Tumor
Cell Proliferation / drug effects
Flavones / chemical synthesis,  chemistry,  pharmacology
HSP90 Heat-Shock Proteins / antagonists & inhibitors,  metabolism
Isoflavones / chemical synthesis,  chemistry*,  pharmacology*
Molecular Structure
Novobiocin / chemical synthesis,  chemistry*,  pharmacology*
Grant Support
CA120458/CA/NCI NIH HHS; U01 CA120458/CA/NCI NIH HHS; U01 CA120458-04/CA/NCI NIH HHS
Reg. No./Substance:
0/Antineoplastic Agents; 0/Flavones; 0/HSP90 Heat-Shock Proteins; 0/Isoflavones; 0/derrubone; 303-81-1/Novobiocin

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