129397-55-3Relevant academic research and scientific papers
Rationally designed 'dipeptoid' analogues of cholecystokinin (CCK): N-terminal structure-affinity relationships of α-methyl-tryptophan derivatives
Eden,Higginbottom,Hill,Horwell,Hunter,Martin,Pritchard,Rahman,Richardson,Roberts
, p. 37 - 45 (2007/10/02)
The structure-affinity relationships (SAR) between the N-terminii of a series of α-methyl-tryptophanylphenethylamide derivatives and the cholecystokinin (CCK) B receptor are discussed. A series of compounds with the general formula R-X-α-methyl-tryptophanylphenethylamide was prepared, where R is a cycloalkyl, a bicycloalkyl or a tricycloalkyl group and X is a urethane, thiourethane, amide, urea or a sulphinamide linking group. The CCK-B receptor binding affinities of these are discussed. The SAR form part of a systematic program for the rational design of 'dipeptoid' analogues of the neuropeptide CCK. Beginning with 1,1-dimethylpropyl (±)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2- [(2-phenylethyl)amino carbamate (IC50 = 4720 nM on CCK-B binding affinity) the N-terminal moiety was systematically changed for groups of varying size, shape and lipophilicity until the optimal N-terminal group was obtained and the favoured linking group chosen, resulting in the compound tricyclo[3.3.1.13,7)]dec-2-yl(R)-[(1H-indol-3-ylmethyl)-1-methyl- 2-oxo-2[(2-phenylethyl)amino]ethyl]carbamate with and IC50 = 32 nM on CCK-B receptor binding affinity.
Cholecystokinin dipeptoid antagonists: Design, synthesis, and anxiolytic profile of some novel CCK-A and CCK-B selective and 'mixed' CCK-A/CCK-B antagonists
Boden,Higginbottom,Hill,Horwell,Hughes,Rees,Roberts,Singh,Suman-Chauhan,Woodruff
, p. 552 - 565 (2007/10/02)
The design, synthesis, and structure-activity relationships (SAR) for the development of selective dipeptoid ligands for both of the cholecystokinin (CCK) receptor subtypes CCK-A and CCK-B are described. The SAR developed is used to design a ligand with e
α-Methyl tryptophanylphenylalanines and their arylethylamine 'dipeptoid' analogues of the tetrapeptide cholecystokinin (30-33)
Horwell,Birchmore,Boden,Higginbottom,Ping Ho,Hughes,Hunter,Richardson
, p. 53 - 60 (2007/10/02)
A series of N-alkyl carbamate blocked α-Me-Trp-Phe and α-Me-Trp-phenethylamides has been identified as 'dipeptoid' analogues of CCK-4 (CCK 30-33). These compounds have micromolar affinity for the type-B central CCK receptor, some of which increase the fir
