Muto Y, Ichikawa H, Seiki M, Shirataki Y, Yokoe I, Komatsu M
Central Research Laboratories, Zeria Pharmaceutical Co., Ltd., Saitama, Japan.
Yakugaku Zasshi. 1994 Dec;114(12):995-1004. doi: 10.1248/yakushi1947.114.12_995.
It was found that gamma-irigermanal, obtained from the methanol extract of root of Iris germanica, exhibited a potent antiulcer activity. Therefore, this compound was selected as a lead-compound, and related compounds were synthesized and tested for antiulcer activities. It was found that (+/-) ethyl 2-[2-(3-hydroxypropyl)-4-oxocyclohexylidene]- propionate (1) had excellent antiulcer activities. Then phenylpropanol derivatives, obtained by changing from cyclohexane ring of 1 to benzene ring, were synthesized and tested for antiulcer activities in order to study structure activity relationships. As a result, (+/-) ethyl 2-[2-(3-hydroxypropyl)-4,5-dimethoxy-phenyl]propionate (2b) and (+/-) 3-[2-(3-hydroxypropyl)-4,5-dimethoxyphenyl]-2-butanone (5) were shown to have antiulcer activities.
结果发现，从德国鸢尾根部甲醇提取物中获得的γ-鸢尾酮具有很强的抗溃疡活性。因此，该化合物被选为先导化合物，并合成了相关化合物并测试其抗溃疡活性。结果发现，(±)-2-[2-(3-羟丙基)-4-氧代环己叉基]丙酸乙酯(1)具有优异的抗溃疡活性。然后，通过将1的环己烷环变为苯环得到苯丙醇衍生物，并测试其抗溃疡活性以研究构效关系。结果表明，(±)-2-[2-(3-羟丙基)-4,5-二甲氧基苯基]丙酸乙酯(2b)和(±)-3-[2-(3-羟丙基)-4,5-二甲氧基苯基]-2-丁酮(5)具有抗溃疡活性。
