Design, synthesis, and structural analysis of phenylpropanoic acid-type PPARgamma-selective agonists: discovery of reversed stereochemistry-activity relationship.

Article Details

Citation

Ohashi M, Oyama T, Nakagome I, Satoh M, Nishio Y, Nobusada H, Hirono S, Morikawa K, Hashimoto Y, Miyachi H

Design, synthesis, and structural analysis of phenylpropanoic acid-type PPARgamma-selective agonists: discovery of reversed stereochemistry-activity relationship.

J Med Chem. 2011 Jan 13;54(1):331-41. doi: 10.1021/jm101233f. Epub 2010 Dec 3.

PubMed ID
21128600 [ View in PubMed
]
Abstract

Peroxisome proliferator-activated receptor gamma (PPARgamma) is a ligand-mediated transcription factor with roles in glucose, lipid, and lipoprotein homeostasis, and PPARgamma ligands are expected have therapeutic potential in these as well as other areas. We report here the design, synthesis, crystallographic analysis, and computational studies of alpha-benzylphenylpropanoic acid PPARgamma agonists. Interestingly, these compounds show a reversal of the stereochemistry-transactivation activity relationship observed with other phenylpropanoic acid ligands.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
RosiglitazonePeroxisome proliferator-activated receptor gammaEC 50 (nM)43N/AN/ADetails