Potent imidazole and triazole CB1 receptor antagonists related to SR141716

被引:75
作者
Dyck, B
Goodfellow, VS
Phillips, T
Grey, J
Haddach, M
Rowbottom, M
Naeve, GS
Brown, B
Saunders, J
机构
[1] Neurocrine Biosci Inc, Dept Med Chem, San Diego, CA 92121 USA
[2] Neurocrine Biosci Inc, Dept Mol Biol & Pharmacol, San Diego, CA 92121 USA
关键词
D O I
10.1016/j.bmcl.2003.12.068
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Diarylimidazolecarboxamides and diaryltriazolecarboxamides related to SR141716 were synthesized and tested for binding to the human CB1 receptor. Suitably substituted imidazoles are comparably potent to the clinical candidate, whereas the analogous triazoles are less so due to the absence of an additional substituent on the azole ring. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1151 / 1154
页数:4
相关论文
共 27 条
  • [1] NEUROBIOLOGY OF MARIJUANA ABUSE
    ABOOD, ME
    MARTIN, BR
    [J]. TRENDS IN PHARMACOLOGICAL SCIENCES, 1992, 13 (05) : 201 - 206
  • [2] Barth F, 1999, CURR MED CHEM, V6, P745
  • [3] BARTH F, 1997, Patent No. 5624941
  • [4] A selective inverse agonist for central cannabinoid receptor inhibits mitogen-activated protein kinase activation stimulated by insulin or insulin-like growth factor 1 - Evidence for a new model of receptor/ligand interactions
    Bouaboula, M
    Perrachon, S
    Milligan, L
    Canat, X
    RinaldiCarmona, M
    Portier, M
    Barth, F
    Calandra, B
    Pecceu, F
    Lupker, J
    Maffrand, JP
    LeFur, G
    Casellas, P
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (35) : 22330 - 22339
  • [5] ISOLATION AND STRUCTURE OF A BRAIN CONSTITUENT THAT BINDS TO THE CANNABINOID RECEPTOR
    DEVANE, WA
    HANUS, L
    BREUER, A
    PERTWEE, RG
    STEVENSON, LA
    GRIFFIN, G
    GIBSON, D
    MANDELBAUM, A
    ETINGER, A
    MECHOULAM, R
    [J]. SCIENCE, 1992, 258 (5090) : 1946 - 1949
  • [6] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
    FARINA, V
    KRISHNAN, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595
  • [7] Cannabinoid receptors and their endogenous agonists
    Felder, CC
    Glass, M
    [J]. ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1998, 38 : 179 - 200
  • [8] Synthesis and structure-activity relationships of amide and hydrazide analogues of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716)
    Francisco, MEY
    Seltzman, HH
    Gilliam, AF
    Mitchell, RA
    Rider, SL
    Pertwee, RG
    Stevenson, LA
    Thomas, BF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) : 2708 - 2719
  • [9] HOLLISTER LE, 1986, PHARMACOL REV, V38, P1
  • [10] Azido- and isothiocyanato-substituted aryl pyrazoles bind covalently to the CB1 cannabinoid receptor and impair signal transduction
    Howlett, AC
    Wilken, GH
    Pigg, JJ
    Houston, DB
    Lan, RX
    Liu, Q
    Makriyannis, A
    [J]. JOURNAL OF NEUROCHEMISTRY, 2000, 74 (05) : 2174 - 2181