Design and synthesis of α,β-unsaturated carbonyl compounds as potential ACE inhibitors

被引:23
作者
Choo, HYP [1 ]
Peak, KH
Park, J
Kim, DH
Chung, HS
机构
[1] Ewha Womans Univ, Sch Pharm, Seoul 120750, South Korea
[2] Korea Inst Sci & Technol, Doping Control Ctr, Seoul 130650, South Korea
关键词
alpha; beta-unsaturated amides; angiotensin converting enzyme inhibitor irreversible inhibitors;
D O I
10.1016/S0223-5234(00)00158-6
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The alpha,beta-unsaturated amide that is incorporated into the basic structural frame of a simple substrate molecule of angiotensin converting enzyme was found to serve as a Michael acceptor for the catalytic carboxylate of Glu-127, inhibiting the enzyme irreversibly. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
引用
收藏
页码:643 / 648
页数:6
相关论文
共 13 条
[1]   Epoxyalkanoyls as novel ACE inhibitors [J].
Choo, HYP ;
Yoon, HR ;
Park, HS ;
Kim, DH ;
Park, J ;
Kim, J .
ARCHIVES OF PHARMACAL RESEARCH, 1998, 21 (02) :168-173
[2]   DESIGN OF POTENT COMPETITIVE INHIBITORS OF ANGIOTENSIN-CONVERTING ENZYME - CARBOXYALKANOYL AND MERCAPTOALKANOYL AMINO-ACIDS [J].
CUSHMAN, DW ;
CHEUNG, HS ;
SABO, EF ;
ONDETTI, MA .
BIOCHEMISTRY, 1977, 16 (25) :5484-5491
[3]  
CUSHMAN DW, 1978, PROG CARDIOVASC DIS, V21, P175
[4]  
GHOSH SS, 1991, J BIOL CHEM, V266, P8759
[5]   Properties of analogues of an intermediate in the process of mechanism-based inactivation of carboxypeptidase A [J].
Ghosh, SS ;
Dakoji, S ;
Tanaka, Y ;
Cho, YJ ;
Mobashery, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (09) :1487-1492
[6]   DESIGN OF A NOVEL TYPE OF ZINC-CONTAINING PROTEASE INHIBITOR [J].
KIM, DH ;
KIM, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3200-3202
[7]   (MERCAPTOPROPANOYL)INDOLINE-2-CARBOXYLIC ACIDS AND RELATED-COMPOUNDS AS POTENT ANGIOTENSIN CONVERTING ENZYME-INHIBITORS AND ANTIHYPERTENSIVE AGENTS [J].
KIM, DH ;
GUINOSSO, CJ ;
BUZBY, GC ;
HERBST, DR ;
MCCAULLY, RJ ;
WICKS, TC ;
WENDT, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (03) :394-403
[8]  
KOSTIS JB, 1987, ANGIOTENSIN CONVERTI, P21
[9]   Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediols via enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones [J].
Lee, N ;
Kim, YW ;
Chang, K ;
Kim, KH ;
Jew, SS ;
Kim, DK .
TETRAHEDRON LETTERS, 1996, 37 (14) :2429-2432
[10]   DESIGN OF SPECIFIC INHIBITORS OF ANGIOTENSIN-CONVERTING ENZYME - NEW CLASS OF ORALLY ACTIVE ANTIHYPERTENSIVE AGENTS [J].
ONDETTI, MA ;
CUSHMAN, DW .
SCIENCE, 1977, 196 (4288) :441-444