Discovery of azetidinone acids as conformationally-constrained dual PPARα/γ agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 1939-1944

  Wang, Wei ^a   Devasthale, Pratik ^a   Farrelly, Dennis ^a   Gu, Liqun ^a   Harrity, Thomas ^a   Cap, Michael ^a   Chu, Cuixia ^a   Kunselman, Lori ^a   Morgan, Nathan ^a   Ponticiello, Randy ^a   Zebo, Rachel ^a   Zhang, Litao ^a   Locke, Kenneth ^a   Lippy, Jonathan ^a   O'Malley, Kevin ^a   Hosagrahara, Vinayak ^a   Zhang, Lisa ^a   Kadiyala, Pathanjali ^a   Chang, Chiehying ^a   Muckelbauer, Jodi ^a   Doweyko, Arthur M ^a   Zahler, Robert ^a   Ryono, Denis ^a   Hariharan, Narayanan ^a   Cheng, Peter T W ^a   more..

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Antidiabetic azetidinones; Boronic acid coupling; Conformational constraint; Dual PPAR agonists; PPAR

Indexed keywords

5 (2,4 DIOXO 5 THIAZOLIDINYLMETHYL) 2 METHOXY N [4 (TRIFLUOROMETHYL)BENZYL]BENZAMIDE; AZETIDINONE DERIVATIVE; FENOFIBRATE; GEMFIBROZIL; GW 2331; IMIGLITAZAR; MURAGLITAZAR; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PIOGLITAZONE; ROSIGLITAZONE; TESAGLITAZAR; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; ARYLATION; CONTROLLED STUDY; DIABETES MELLITUS; DRUG CONFORMATION; DRUG LIVER LEVEL; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DYSLIPIDEMIA; FEMALE; MOUSE; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TRIACYLGLYCEROL BLOOD LEVEL;

ADMINISTRATION, ORAL; ANIMALS; AZETIDINES; BIOLOGICAL AVAILABILITY; COPPER; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 ENZYME SYSTEM; DIABETES MELLITUS, EXPERIMENTAL; DYSLIPIDEMIAS; ETHER-A-GO-GO POTASSIUM CHANNELS; GLUCOSE; MICE; MICE, MUTANT STRAINS; MOLECULAR STRUCTURE; PPAR ALPHA; PPAR GAMMA; PROTEIN CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIGLYCERIDES;

EID: 40749086322     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.126     Document Type: Article

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28. Following Scheme 1
29. Following Scheme 2, via t-Bu ester (+)-23b
30. Following Scheme 2, via t-Bu ester (-)-23b
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32. Following Scheme 2, via racemic Me ester 23.
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