SYNTHESIS OF 1-((S)-3-ACETYLTHIO-2-METHYLPROPANOYL)-L-PROPYL-L-PHENYLALANINE (ALACEPRIL) AND ONE OF ITS ACTIVE METABOLITES, THE DESACETYL DERIVATIVE (DU-1227)

被引：6

作者：

SAWAYAMA, T ^{[1
]}

ITOKAWA, A ^{[1
]}

SHIMADA, K ^{[1
]}

DOI, Y ^{[1
]}

KIMURA, Y ^{[1
]}

NISHIMURA, H ^{[1
]}

机构：

[1] DAINIPPON PHARMACEUT CO LTD, DEPT CHEM TECHNOL, FUKUSHIMA, OSAKA 553, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 02期

关键词：

1-formyl-L-proline; active metabolite; alacepril; antihypertensive agent; captopril; chloral; conformation; DU-1219; DU-1227; hydrogen bond;

D O I：

10.1248/cpb.38.529

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of l-((S)-3-acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine 1 (alacepril, code name: DU-1219), a clinically used antihypertensive agent, and one of its active metabolites, l-((5)-3-mercapto-2-methylpropanoyl)-L-prolyl-L-phenylalanine 2 (code name: DU-1227), is described. The application of chloral to the yV-formylation of L-proline is also described. The presence of an intramolecular hydrogen bond in the trans conformer of 1 in solution is suggested on the basis of spectroscopic examinations of 1 and its ethyl ester 4. © 1990, The Pharmaceutical Society of Japan. All rights reserved.

引用

页码：529 / 531

页数：3

共 14 条

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