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CAS号74431-50-8 3-苯甲酰硫基-2-甲基丙酸 | CAS号98-88-4 苯甲酰氯 | CAS号75172-11-1 (S)-3-mercapto-...

3-苯甲酰硫基-2-甲基丙酸 反应生成 (S)-(-)-3-苯甲酰巯基-2-甲基丙酸
参考文献:Studies On Angiotensin-Converting Enzyme Inhibitors. I. Syntheses And Angiotensinconverting Enzyme Inhibitory Activity Of 2-(3-Mercaptopropionyl)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid Derivatives.
标题:Studies On Angiotensin-Converting Enzyme Inhibitors. I. Syntheses And Angiotensinconverting Enzyme Inhibitory Activity Of 2-(3-Mercaptopropionyl)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid Derivatives.
摘要:(3S)-2-[(2S)-3-巯基-2-甲基丙酰基]-1,2,3,4-四氢异喹啉-3-羧酸[(3S),(2S)-6A]是通过(3S)-1,2,3,4-四氢异喹啉-3-羧酸叔丁基酯[(3S)-2A]或苄基酯[(3S)-2B]与3-苯甲酰硫-2-甲基丙酰氯(3A)反应制备而成,随后通过分馏结晶去除保护基团.通过对由6A衍生的噻唑烯[4,3-B]异喹啉化合物(7)进行x射线衍射分析,确认了(3S),(2S)-6A的绝对构型.使用光学活性的苯丙氨酸酰胺作为分解剂完成了3-苯甲酰硫-2-甲基丙酸(8)的分解.通过(3S)-或(3R)-2B与光学活性3A反应制备了(3S),(2S)-6A的其他光学异构体.评估了每种6A异构体的体外ace抑制活性.其中,(3S),(2S)-6A被发现是最有效的抑制剂,Ic50值为8.6x10^-9M.化合物(3S),(2S)-6A在该显混合型麻醉大鼠口服给药后,诱导了对血管紧张素i的加压反应的剂量依赖性抑制.此外,(3S),(2S)-6A显著降低了肾性高血压大鼠(Rhr)和自发性高血压大鼠(Shr)的收缩压.(3S),(2S)-6A的体内ace抑制活性和降压效果与卡托普利相当.
DOI:10.1248/cpb.31.570

专利信息

专利号:US-5420037-A
优先权日:1989-09-26
标 题:Process for separation of enantiomeric 3-mercapto-2-substituted alkanoic acid using lipase P30 and synthesis of captopril type compounds
发明人：HOWELL JEFFREY M; PATEL RAMESH N; SZARKA LASZLO J
权利人:SQUIBB & SONS INC
摘要:S-enantiomers of the formula I result from the reaction of a racemic form of compound I with an alcohol in the presence of an enzyme capable of selectively esterifying the R-enantiomers of the racemic compound.