New generation dopaminergic agents.: 7.: Heterocyclic bioisosteres that exploit the 3-OH-phenoxyethylamine D2 template

被引:11
作者
Mewshaw, RE
Nelson, JA
Shah, US
Shi, XJ
Mazandarani, H
Coupet, J
Marquis, K
Brennan, JA
Andree, TH
机构
[1] Wyeth Ayerst Res Labs, Goobal Chem Sci Dept, Princeton, NJ 08543 USA
[2] Wyeth Ayerst Res Labs, CNS Disorders Dept, Princeton, NJ 08543 USA
关键词
D O I
10.1016/S0960-894X(99)00434-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of several bioisosteric analogs based on the 3-OH-phenoxyethylamine dopamine D-2 agonist template (i.e., 3) is described. The benzimidazol-2-ones and benzthioimidazol-2-ones (7-10) and 2-trifluoromethyl-benzimidazole (13) were observed to have excellent affinity for the Dp receptor. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2593 / 2598
页数:6
相关论文
共 10 条
[1]   DOPAMINE RECEPTOR AGONISTS - MECHANISMS UNDERLYING AUTORECEPTOR SELECTIVITY .2. THEORETICAL CONSIDERATIONS [J].
CLARK, D ;
HJORTH, S ;
CARLSSON, A .
JOURNAL OF NEURAL TRANSMISSION, 1985, 62 (3-4) :171-207
[2]   DOPAMINE-RECEPTORS - FUNCTIONS, SUBTYPES AND EMERGING CONCEPTS [J].
KAISER, C ;
JAIN, T .
MEDICINAL RESEARCH REVIEWS, 1985, 5 (02) :145-229
[3]  
LAHTI RA, 1992, MOL PHARMACOL, V42, P432
[4]   DOPAMINE HYPOTHESIS OF SCHIZOPHRENIA - REVIEW [J].
MELTZER, HY ;
STAHL, SM .
SCHIZOPHRENIA BULLETIN, 1976, 2 (01) :19-76
[5]   New generation dopaminergic agents.: 6.: Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D2 template [J].
Mewshaw, RE ;
Webb, MB ;
Marquis, KL ;
McGaughey, GB ;
Shi, XJ ;
Wasik, T ;
Scerni, R ;
Brennan, JA ;
Andree, TH .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (11) :2007-2020
[6]   New generation dopaminergic agents.: 2.: Discovery of 3-OH-phenoxyethnamine and 3-OH-N1-phenylpiperazine dopaminergic templates [J].
Mewshaw, RE ;
Husbands, M ;
Gildersleeve, ES ;
Webb, MB ;
Shi, XJ ;
Mazandarani, H ;
Cockett, MI ;
Ochalski, R ;
Brennan, JA ;
Abou-Gharbia, M ;
Marquis, K ;
McGaughey, GB ;
Coupet, J ;
Andree, TH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (03) :295-300
[7]   New generation dopaminergic agents .1. Discovery of a novel scaffold which embraces the D2 agonist pharmacophore.: Structure-activity relationships of a series of 2-(aminomethyl)chromans [J].
Mewshaw, RE ;
Kavanagh, J ;
Stack, G ;
Marquis, KL ;
Shi, XJ ;
Kagan, MZ ;
Webb, MB ;
Katz, AH ;
Park, A ;
Kang, YH ;
Abou-Gharbia, M ;
Scerni, R ;
Wasik, T ;
Cortes-Burgos, L ;
Spangler, T ;
Brennan, JA ;
Piesla, M ;
Mazandarani, H ;
Cockett, MI ;
Ochalski, R ;
Coupet, J ;
Andree, TH .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4235-4256
[8]   New generation dopaminergic agents 4. Exploiting the 2-methyl chroman scaffold. Synthesis and evaluation of two novel series of 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano[2,3-e]indole and indol-8-one derivatives [J].
Mewshaw, RE ;
Marquis, KL ;
Shi, XJ ;
McGaughey, G ;
Stack, G ;
Webb, MB ;
Abou-Gharbia, M ;
Wasik, T ;
Scerni, R ;
Spangler, T ;
Brennan, JA ;
Mazandarani, H ;
Coupet, J ;
Andree, TH .
TETRAHEDRON, 1998, 54 (25) :7081-7108
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]  
Wasik T. P., 1996, Society for Neuroscience Abstracts, V22, P831