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Design, Synthesis and Biological Study of Pinacolyl Boronate-Substituted Stilbenes as Novel Lipogenic Inhibitors

Design, Synthesis and Biological Study of Pinacolyl Boronate-Substituted Stilbenes as Novel Lipogenic Inhibitors

Bhaskar C Das, Xiaoping Zhao, Xiang-Ying Tang, Fajun Yang

Bioorg Med Chem Lett. 2011 Sep 15;21(18):5638-41.

PMID: 21798740

Abstract:

A pilot library of novel 4,4,5,5-tetramethyl-2-(4-substitutedstyrylphenyl)-1,3,2 dioxaborolane derivatives has been synthesized. 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 3 was treated with various aldehydes in the presence of 3 equiv of (t)BuONa in DMF, and stirred at room temperature for 4-6h to yield the corresponding boron-containing stilbene derivatives in 71-94% yields. Several of them, including BF102 and BF175, have the lipogenesis inhibitory effect by suppressing lipogenic gene expression in mammalian hepatocytes. Further, BF102 also inhibits cholesterol biosynthesis by suppressing HMG-CoA reductase gene expression in hepatocytes. Interestingly, our preliminary in vivo data suggests that BF102 has no significant toxicity in mice at the highest possible dose we can administered. Thus, BF102 is a potential lead for the next generation of lipid-lowering drugs.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793333	4,4,5,5-tetramethyl-2-(3-trifluoromethoxyphenyl)-1,3,2-dioxaborolane			Price

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