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Total synthesis and dual PPARα/γ agonist effects of amorphastilbol and its synthetic derivatives.

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) α/γ 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 PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

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

doi

10.1016/j.bmcl.2012.04.062

subject

Has Abstract

pub_date

2012-06-15 00:00:00

pages

4122-6

issue

12

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)00512-4

journal_volume

22

pub_type

杂志文章

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