白杨素衍生物的合成及其对COX-2催化的前列腺素生成的抑制活性。

Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives.

作者信息

Dao Tran Thanh, Chi Yeon Sook, Kim Jeongsoo, Kim Hyun Pyo, Kim Sanghee, Park Haeil

机构信息

College of Pharmacy, Kangwon National University, Chunchon 200-701, South Korea.

出版信息

Bioorg Med Chem Lett. 2004 Mar 8;14(5):1165-7. doi: 10.1016/j.bmcl.2003.12.087.

DOI:10.1016/j.bmcl.2003.12.087

PMID:14980657

Abstract

A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr(3) in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.

摘要

制备了一系列白杨素衍生物，并评估了它们对环氧合酶-2催化的前列腺素生成的抑制活性。白杨素衍生物分别由2-羟基苯乙酮、2,4-二羟基苯乙酮和2,6-二羟基苯乙酮经2至4步反应制备而成。甲氧基化的白杨素衍生物通过与三溴化硼反应以良好的产率转化为相应的羟基化白杨素衍生物。测定了白杨素衍生物对脂多糖处理的RAW 264.7细胞中前列腺素生成的抑制活性。我们发现具有3',4'-二氯取代基的白杨素衍生物（5e、6e和7e）表现出良好的前列腺素生成抑制活性。