Total synthesis and dual PPARalpha/gamma agonist effects of amorphastilbol and its synthetic derivatives.

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Kim T, Lee W, Jeong KH, Song JH, Park SH, Choi P, Kim SN, Lee S, Ham J

Total synthesis and dual PPARalpha/gamma agonist effects of amorphastilbol and its synthetic derivatives.

Bioorg Med Chem Lett. 2012 Jun 15;22(12):4122-6. doi: 10.1016/j.bmcl.2012.04.062. Epub 2012 Apr 19.

PubMed ID
22579420 [ View in PubMed
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Abstract

Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer [corrected] seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) alpha/gamma agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARalpha/gamma transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARalpha/gamma agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
CardarinePeroxisome proliferator-activated receptor deltaEC 50 (nM)1.2N/AN/ADetails
TroglitazonePeroxisome proliferator-activated receptor gammaEC 50 (nM)400N/AN/ADetails
TroglitazonePeroxisome proliferator-activated receptor gammaIC 50 (nM)300N/AN/ADetails