Document Detail

Discovery of a novel class of 2-mercaptohexanoic acid derivatives as highly active PPARalpha agonists.
MedLine Citation:
PMID:  19556125     Owner:  NLM     Status:  MEDLINE    
A novel and robust scaffold for highly active PPARalpha agonists based on the 2-mercaptohexanoic acid substructure is presented. Systematic structural variation of the substitution pattern of the phenolic backbone yielded detailed SAR especially of ortho and meta substituents. We corroborated the importance of the sulfur atom as well as of the n-butyl chain for PPARalpha activity in the 2-mercaptohexanoic acid head group by preparation of carbon analogs and alpha-unsubstituted derivatives. Compound 10 represents a low nano molar active PPARalpha activator with excellent selectivity towards PPARgamma.
Heiko Zettl; Ramona Steri; Michael Lämmerhofer; Manfred Schubert-Zsilavecz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-05-18
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  19     ISSN:  1464-3405     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2009 Aug 
Date Detail:
Created Date:  2009-07-14     Completed Date:  2009-12-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  4421-6     Citation Subset:  IM    
Goethe-University Frankfurt, Institute of Pharmaceutical Chemistry/ZAFES/LiFF, Max-von-Laue-Str. 9, D-60348 Frankfurt/M., Germany.
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MeSH Terms
Carbon / chemistry
Chemistry, Organic / methods
Chemistry, Pharmaceutical / methods*
Combinatorial Chemistry Techniques
Drug Design
Drug Evaluation, Preclinical
Hexanoic Acids / chemical synthesis*,  pharmacology
Models, Chemical
Molecular Structure
PPAR alpha / agonists*,  chemistry
Phenol / chemistry
Structure-Activity Relationship
Sulfhydryl Compounds / chemical synthesis*,  pharmacology
Sulfur / chemistry
Reg. No./Substance:
0/Hexanoic Acids; 0/PPAR alpha; 0/Sulfhydryl Compounds; 108-95-2/Phenol; 7440-44-0/Carbon; 7704-34-9/Sulfur

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