Document Detail

Design and synthesis of novel oxazole containing 1,3-dioxane-2-carboxylic acid derivatives as PPAR alpha/gamma dual agonists.
MedLine Citation:
PMID:  18625559     Owner:  NLM     Status:  MEDLINE    
A few novel 1,3-dioxane carboxylic acid derivatives were designed and synthesized to aid in the characterization of PPAR alpha/gamma dual agonists. Structural requirements for PPARalpha/gamma dual agonism of 1,3-dioxane carboxylic acid derivatives included the structural similarity with potent glitazones in fibric acid chemotype. The compounds with this pharmacophore and substituted oxazole as a lipophilic heterocyclic tail were synthesized and evaluated for their in vitro PPAR agonistic potential and in vivo hypoglycemic and hypolipidemic efficacy in animal models. Lead compound 2-methyl-c-5-[4-(5-methyl-2-(4-methylphenyl)-oxazol-4-ylmethoxy)-benzyl]-1,3-dioxane-r-2-carboxylic acid 13b exhibited potent hypoglycemic, hypolipidemic and insulin sensitizing effects in db/db mice and Zucker fa/fa rats.
Harikishore Pingali; Mukul Jain; Shailesh Shah; Pankaj Makadia; Pandurang Zaware; Ashish Goel; Megha Patel; Suresh Giri; Harilal Patel; Pankaj Patel
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Publication Detail:
Type:  Journal Article     Date:  2008-06-28
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  16     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2008 Aug 
Date Detail:
Created Date:  2008-08-11     Completed Date:  2008-11-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  7117-27     Citation Subset:  IM    
Zydus Research Centre, Sarkhej-Bavla N.H 8A Moraiya, Ahmedabad 382210, India.
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MeSH Terms
Carboxylic Acids / chemistry*,  pharmacology*
Diabetes Mellitus / drug therapy
Drug Design
Hypoglycemic Agents / chemistry,  pharmacology
Mice, Inbred NOD
Molecular Structure
Oxazoles / chemistry*,  pharmacology*
PPAR alpha / agonists*
PPAR gamma / agonists*
Rats, Zucker
Structure-Activity Relationship
Reg. No./Substance:
0/Carboxylic Acids; 0/Hypoglycemic Agents; 0/Oxazoles; 0/PPAR alpha; 0/PPAR gamma

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