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.
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.
Maeda
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S
New Drug Research Laboratories, Kanebo Co., Ltd., Osaka, Japan.
Masuda
H
H
Tokoroyama
T
T
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001205:Ascorbic Acid / Q000494:pharmacology; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar
D000975:Antioxidants; D010636:Phenols; C092642:methyl-3-(4-hydroxy-2-methoxyphenyl)propenoate; D001205:Ascorbic Acid