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通过氧化偶联反应制备生物活性木脂素的研究。III. 由(E)-3-(4-羟基-2-甲氧基苯基)丙烯酸甲酯的氧化偶联反应合成多酚苯并呋喃和香豆雌酚衍生物及其对脂质过氧化的抑制作用。

Studies on the preparation of bioactive lignans by oxidative coupling reaction. III. Synthesis of polyphenolic benzofuran and coumestan derivatives by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate and their inhibitory effect on lipid peroxidation.

作者信息

Maeda S, Masuda H, Tokoroyama T

机构信息

New Drug Research Laboratories, Kanebo Co., Ltd., Osaka, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1994 Dec;42(12):2536-45. doi: 10.1248/cpb.42.2536.

DOI:10.1248/cpb.42.2536
PMID:7697770
Abstract

Three dihydrobenzofuran derivatives 11, 19, 22, a Pummerer's ketone 20 and a dimeric phenylpropanoid 24 were synthesized by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate 10, which was prepared from umbelliferone. The major product 11 was converted into its acetate 21 and schizotenuin D analogs 27, 28, 29. A new coumestan derivative 13 was synthesized from 29. Ten synthetic compounds thus obtained were tested for inhibitory effects on lipid peroxidation in rat brain homogenate.

摘要

通过氧化偶联反应,由伞形酮制备的(E)-3-(4-羟基-2-甲氧基苯基)丙烯酸甲酯10合成了三种二氢苯并呋喃衍生物11、19、22、一种普默勒酮20和一种二聚体苯丙素24。主要产物11被转化为其乙酸酯21和裂环马钱子素D类似物27、28、29。由29合成了一种新的香豆雌酚衍生物13。对由此得到的十种合成化合物进行了在大鼠脑匀浆中对脂质过氧化抑制作用的测试。

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