Novel constrained CCK-B dipeptoid antagonists derived from pipecolic acid

被引:27
作者
Bellier, B [1 ]
Da Nascimento, S [1 ]
Meudal, H [1 ]
Gincel, E [1 ]
Roques, BP [1 ]
Garbay, C [1 ]
机构
[1] UFR Sci Pharmaceut & Biol, CNRS URA D1500, INSERM U266, Dept Pharmacochim Mol & Struct, F-75270 Paris 06, France
关键词
cholecystokinin; peptoids; antagonists;
D O I
10.1016/S0960-894X(98)00231-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of 4-substituted pipecolic acid derivatives was prepared and incorporated into dipeptoids. The resulting products behave as moderately potent CCK-B antagonists but their constrained structure and its comparison with structurally related compounds yield valuable information about the conformational requirements for optimal recognition of the CCK-B receptor by antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1419 / 1424
页数:6
相关论文
共 15 条
[1]   NOVEL CHOLECYSTOKININ RECEPTOR LIGANDS OXOPIPERAZINES DERIVED FROM BOC-CCK-4 [J].
BATT, AR ;
KENDRICK, DA ;
MATHEWS, E ;
ROOKER, DP ;
RYDER, H ;
SEMPLE, G ;
SZELKE, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (07) :867-872
[2]   Synthesis and biological properties of new constrained CCK-B antagonists: Discrimination of two affinity states of the CCK-B receptor on transfected CHO cells [J].
Bellier, B ;
McCortTranchepain, I ;
Ducos, B ;
Danascimento, S ;
Meudal, H ;
Noble, F ;
Garbay, C ;
Roques, BP .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3947-3956
[3]   CHOLECYSTOKININ PEPTIDOMIMETICS AS SELECTIVE CCK-B ANTAGONISTS - DESIGN, SYNTHESIS, AND IN-VITRO AND IN-VIVO BIOCHEMICAL-PROPERTIES [J].
BLOMMAERT, AGS ;
WENG, JH ;
DORVILLE, A ;
MCCORT, I ;
DUCOS, B ;
DURIEUX, C ;
ROQUES, BP .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2868-2877
[4]   BIOLOGICAL ACTIONS OF CHOLECYSTOKININ [J].
CRAWLEY, JN ;
CORWIN, RL .
PEPTIDES, 1994, 15 (04) :731-755
[5]   HETEROGENEITY OF CCK-B RECEPTORS INVOLVED IN ANIMAL-MODELS OF ANXIETY [J].
DERRIEN, M ;
MCCORTTRANCHEPAIN, I ;
DUCOS, B ;
ROQUES, BP ;
DURIEUX, C .
PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1994, 49 (01) :133-141
[6]   OCCURRENCE OF 2 CHOLECYSTOKININ BINDING-SITES IN GUINEA-PIG BRAIN CORTEX [J].
DURIEUX, C ;
COPPEY, M ;
ZAJAC, JM ;
ROQUES, BP .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1986, 137 (03) :1167-1173
[7]   Preparation of (2S,4R)-4-hydroxypipecolic acid and derivatives [J].
Gillard, J ;
Abraham, A ;
Anderson, PC ;
Beaulieu, PL ;
Bogri, T ;
Bousquet, Y ;
Grenier, L ;
Guse, I ;
Lavallee, P .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2226-2231
[8]   Synthesis of gamma-oxo alpha-amino acids from L-aspartic acid [J].
Golubev, AS ;
Sewald, N ;
Burger, K .
TETRAHEDRON, 1996, 52 (47) :14757-14776
[9]   CCK-4 restricted analogues containing a 3-oxoindolizidine skeleton [J].
GonzalezMuniz, R ;
Dominguez, MJ ;
MartinMartinez, M ;
Herranz, R ;
GarciaLopez, MT ;
Barber, A ;
Ballaz, S ;
DelRio, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (08) :967-972
[10]  
Guttmann S., 1958, Helv. Chim. Acta, V41, P1852