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

页码：221 / 233

页数：12

共 50 条

[31] Are biological actions of neurokinin A in the adult brain mediated by a cross-talk between the NK1 and NK2 receptors?
Tauer, Ulrike
Zhao, Yi
Hunt, Steven P.
Culman, Juraj
NEUROPHARMACOLOGY, 2012, 63 (06) : 958 - 965
[32] Comparative distribution of NK1, NK2, and NK3 receptors in the rat brainstem auditory nuclei
Hafidi, A
Beurg, M
Bouleau, Y
Dulon, D
BRAIN RESEARCH, 2002, 947 (02) : 299 - 306
[33] NK1, NK2 and NK3 tachykinin receptor localization and tachykinin distribution in the ileum of the mouse
M. -G. Vannucchi
M. -S. Faussone-Pellegrini
Anatomy and Embryology, 2000, 202 : 247 - 255
[34] Role of tachykinin NK1, NK2 and NK3 receptors in the modulation of visceral hypersensitivity in the rat
Gaudreau, GA
Plourde, V
NEUROSCIENCE LETTERS, 2003, 351 (02) : 59 - 62
[35] NK1/NK2/NK3/NKr1 paradigm in normal pregnancy and spontaneous abortion
Saito, S.
Myojo, S.
Nakashima, A.
Shiozaki, A.
JOURNAL OF REPRODUCTIVE IMMUNOLOGY, 2006, 71 (02) : 141 - 141
[36] Postnatal development of NK1, NK2, and NK3 neurokinin receptors expression in the rat retina
Oyamada, H
Takatsuji, K
Senba, E
Mantyh, PW
Tohyama, M
DEVELOPMENTAL BRAIN RESEARCH, 1999, 117 (01): : 59 - 70
[37] Tachykinins regulate intestinal peristalsis via NK1 and NK2, but not NK3, receptors.
Lippe, IT
Holzer, P
GASTROENTEROLOGY, 1997, 112 (04) : A777 - A777
[38] NK1, NK2 and NK3 tachykinin receptor localization and tachykinin distribution in the ileum of the mouse
Vannucchi, MG
Faussone-Pellegrini, MS
ANATOMY AND EMBRYOLOGY, 2000, 202 (03): : 247 - 255
[39] NK1 and NK2 receptor gene and protein expression in inflammatory bowel disease (IBD).
Calabro, A
Renzi, D
Pellegrini, B
Savini, L
Tonelli, F
Surrenti, C
GASTROENTEROLOGY, 1999, 116 (04) : A676 - A676
[40] Membrane-induced structure of scyliorhinin I: A dual NK1/NK2 agonist
Dike, A
Cowsik, SM
BIOPHYSICAL JOURNAL, 2005, 88 (05) : 3592 - 3600

← 1 2 3 4 5 →