| Discovery of a novel class of 2-mercaptohexanoic acid derivatives as highly active PPARalpha agonists. | |
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MedLine Citation:
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PMID: 19556125 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Heiko Zettl; Ramona Steri; Michael Lämmerhofer; Manfred Schubert-Zsilavecz |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2009-05-18 |
Journal Detail:
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Title: Bioorganic & medicinal chemistry letters Volume: 19 ISSN: 1464-3405 ISO Abbreviation: Bioorg. Med. Chem. Lett. Publication Date: 2009 Aug |
Date Detail:
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Created Date: 2009-07-14 Completed Date: 2009-12-07 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9107377 Medline TA: Bioorg Med Chem Lett Country: England |
Other Details:
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Languages: eng Pagination: 4421-6 Citation Subset: IM |
Affiliation:
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Goethe-University Frankfurt, Institute of Pharmaceutical Chemistry/ZAFES/LiFF, Max-von-Laue-Str. 9, D-60348 Frankfurt/M., Germany. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Carbon
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chemistry Chemistry, Organic / methods Chemistry, Pharmaceutical / methods* Combinatorial Chemistry Techniques Drug Design Drug Evaluation, Preclinical Hexanoic Acids / chemical synthesis*, pharmacology Humans Models, Chemical Molecular Structure PPAR alpha / agonists*, chemistry Phenol / chemistry Structure-Activity Relationship Sulfhydryl Compounds / chemical synthesis*, pharmacology Sulfur / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Hexanoic Acids; 0/PPAR alpha; 0/Sulfhydryl Compounds; 108-95-2/Phenol; 7440-44-0/Carbon; 7704-34-9/Sulfur |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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