Synthesis and biological evaluation of conformationally restricted derivatives of tryptophan as NK1/NK2 ligands

被引:3
|
作者
Millet R. [1 ]
Goossens J.-F. [1 ,2 ]
Bertrand-Caumont K. [1 ,3 ]
Chavatte P. [1 ]
Houssin R. [1 ]
Hénichart J.-P. [1 ]
机构
[1] Institut de Chimie Pharmaceutique, Université de Lille 2, Droit et Santé, F-59006 Lille Cedex
[2] Laboratoire de Chimie Analytique, Faculté de Pharmacie, Université de Lille 2, F-59006 Lille Cedex
[3] UCB S.A. Pharma Sector, Chemin du Foriest
来源
Letters in Peptide Science | 1999年 / 6卷 / 4期
关键词
Neurokinin A; Substance P; Tachykinins; Tetrahydro-β-; carboline; Tetrahydrocarbazole;
D O I
10.1023/A:1008844323931
中图分类号
学科分类号
摘要
Chemical modifications on the NK1 competitive antagonist L-732,138, with a view to creating a dual NK1/NK2 ligand, led to the tryptophan derivative 1 possessing the protected Gly-Leu sequence of the C-terminus of substance P and neurokinin A. Modifications in the nature of the carbamate function increased the selectivity for the NK1 receptor, whereas the inclusion of the indole moiety in β-carboline or carbazole rings decreased the affinity for both receptors. Free indolylmethyl and Cbz carbamate groups were shown to be essential for NK2 affinity.
引用
收藏
页码:221 / 233
页数:12
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