Solid-phase synthesis of hybrid thiazolidinedione-fatty acid PPARγ ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 19, 1997, Pages 2491-2496

  Tomkinson, Nicholas C O ^a   Sefler, Andrea M ^a   Plunket, Kelli D ^a   Blanchard, Steven G ^a   Parks, Derek J ^a   Willson, Timothy M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; FATTY ACID DERIVATIVE; HORMONE RECEPTOR; LIGAND; PEROXISOME PROLIFERATOR;

ARTICLE; BINDING AFFINITY; DRUG SYNTHESIS; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; RECEPTOR AFFINITY;

EID: 0030798273     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10017-8     Document Type: Article

References (10)

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3. Krey, G.; Braissant, O.; L'Horset, F.; Kalkhoven, E.; Perroud, M.; Parker, M. G.; Wahli, W. Mol. Endocrinol. 1997, 11, 779.
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7. 6 suggested that both ligands adopted turn structures in solution. For TZD (1) NOEs were detected between a proton on the phenoxy ring and the protons adjacent to the side-chain nitrogen, and for FA (2) NOEs were detected between the allylic methylene protons adjacent to the terminal double bonds of the polyene (see below, NOEs observed between protons marked with the closed circles). (figure presented)
8. 2O, and two volumes of EtOAc. The EtOAc fraction was evaporated to yield 4-7 mg (80-90%) of TZD-FA hybrid molecules (4).
9. Potter, B. J.; Sorrentino, D.; Berk, P. D. Annu. Rev. Nutr. 1989, 9, 253.
10. Cantello, B. C. C.; Cawthorne, M. A.; Haigh, D.; Hindley, R. M.; Smith, S. A.; Thurlby, P. Bioorg. Med. Chem. Lett. 1994, 4, 1181.