Incorporation of conformationally constrained phenylalanine derivatives Tic, Sic, Hic and Nic into a cholecystokinin-B/gastrin receptor antagonist

被引:24
作者
Gibson, SE [1 ]
Guillo, N [1 ]
Kalindjian, SB [1 ]
Tozer, MJ [1 ]
机构
[1] JAMES BLACK FDN,LONDON SE24 9JE,ENGLAND
关键词
D O I
10.1016/S0960-894X(97)00211-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The preparation and biological properties of a conformationally constrained series of cholecystokinin-B/gastrin receptor ligands are described. The 9-membered ring (Nic) derivative was found to be as active at these receptors as an unconstrained phenylalanine analogue. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1289 / 1292
页数:4
相关论文
共 20 条
[1]   Topographical amino acid substitution in position 10 of glucagon leads to antagonists partial agonists with greater binding differences [J].
Azizeh, BY ;
Shenderovich, MD ;
Trivedi, D ;
Li, GG ;
Sturm, NS ;
Hruby, VJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (13) :2449-2455
[2]   DEVELOPMENT OF 1,4-BENZODIAZEPINE CHOLECYSTOKININ TYPE-B ANTAGONISTS [J].
BOCK, MG ;
DIPARDO, RM ;
EVANS, BE ;
RITTLE, KE ;
WHITTER, WL ;
GARSKY, VM ;
GILBERT, KF ;
LEIGHTON, JL ;
CARSON, KL ;
MELLIN, EC ;
VEBER, DF ;
CHANG, RSL ;
LOTTI, VJ ;
FREEDMAN, SB ;
SMITH, AJ ;
PATEL, S ;
ANDERSON, PS ;
FREIDINGER, RM .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (26) :4276-4292
[3]   DMT-TIC-OH, a highly selective and potent delta-opioid dipeptide receptor antagonist after systemic administration in the mouse [J].
Capasso, A ;
Guerrini, R ;
Balboni, G ;
Sorrentino, L ;
Temussi, P ;
Lazarus, LH ;
Bryant, SD ;
Salvadori, S .
LIFE SCIENCES, 1996, 59 (08) :PL93-PL98
[4]   CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES [J].
CHUNG, JYL ;
WASICAK, JT ;
ARNOLD, WA ;
MAY, CS ;
NADZAN, AM ;
HOLLADAY, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :270-275
[5]  
FELTOU M, 1995, J PHARMACOL EXP THER, V23, P1071
[6]   PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267
[7]   Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations [J].
Gibson, SE ;
Guillo, N ;
Middleton, RJ ;
Thuilliez, A ;
Tozer, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04) :447-455
[8]   Analysis of variation in L-365,260 competition curves in radioligand binding assays [J].
Harper, EA ;
Roberts, SP ;
Shankley, NP ;
Black, JW .
BRITISH JOURNAL OF PHARMACOLOGY, 1996, 118 (07) :1717-1726
[9]   Pharmacological analysis of the CCKB/gastrin receptors mediating pentagastrin-stimulated gastric acid secretion in the isolated stomach of the immature rat [J].
Hills, DM ;
Gerskowitch, VP ;
Roberts, SP ;
Welsh, NJ ;
Shankley, NP ;
Black, JW .
BRITISH JOURNAL OF PHARMACOLOGY, 1996, 119 (07) :1401-1410
[10]   TOPOGRAPHIC PROBES OF ANGIOTENSIN AND RECEPTOR - POTENT ANGIOTENSIN-II AGONIST CONTAINING DIPHENYLALANINE AND LONG-ACTING ANTAGONISTS CONTAINING BIPHENYLALANINE AND 2-INDAN AMINO-ACID IN POSITION 8 [J].
HSIEH, KH ;
LAHANN, TR ;
SPETH, RC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :898-903