Selective, potent PPARgamma agonists with cyclopentenone core structure.

Article Details

Citation
Copy to clipboard

Otero MP, Perez Santin E, Rodriguez-Barrios F, Vaz B, de Lera AR

Selective, potent PPARgamma agonists with cyclopentenone core structure.

Bioorg Med Chem Lett. 2009 Apr 1;19(7):1883-6. doi: 10.1016/j.bmcl.2009.02.072. Epub 2009 Feb 23.

PubMed ID
19275963 [ View in PubMed
]
Abstract

A series of analogues of the PPARgamma ligand 15-deoxy-Delta(12,14)-PGJ(2) have been synthesized by functionalization of a 5-alkyl-4-hydroxycyclopentenone core structure obtained by Piancatelli rearrangement of precursor furylcarbinol. Transient transactivation assays indicate that analogues 18 and 20 are selective nanomolar agonists of PPARgamma. This subtype selectivity is lost in derivatives (23, 24) with an alkynyl (oct-1-yn) chain at the C3 position, although the cyclopentenone derivative with cis relative configuration (23) showed greater affinity for PPARalpha.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
CardarinePeroxisome proliferator-activated receptor alphaEC 50 (nM)>10000N/AN/ADetails
CardarinePeroxisome proliferator-activated receptor deltaEC 50 (nM)8N/AN/ADetails
RosiglitazonePeroxisome proliferator-activated receptor alphaEC 50 (nM)>10000N/AN/ADetails
RosiglitazonePeroxisome proliferator-activated receptor deltaEC 50 (nM)>10000N/AN/ADetails
RosiglitazonePeroxisome proliferator-activated receptor gammaEC 50 (nM)15N/AN/ADetails