2-BETA-SUBSTITUTED ANALOGS OF COCAINE - SYNTHESIS AND INHIBITION OF BINDING TO THE COCAINE RECEPTOR

被引：89

作者：

LEWIN, AH

GAO, YG

ABRAHAM, P

BOJA, JW

KUHAR, MJ

CARROLL, FI

机构：

[1] RES TRIANGLE INST,POB 12194,RES TRIANGLE PK,NC 27709

[2] NIDA,ADDICT RES CTR,NEUROSCI BRANCH,BALTIMORE,MD 21224

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1992年 / 35卷 / 01期

关键词：

D O I：

10.1021/jm00079a017

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The potencies of a series of 2-beta-substituted cocaine analogues to displace [H-3]-3-beta-fluorophenyl)tropane-2-beta-carboxylic acid methyl ester binding in rat striatal membranes demonstrate the requirement for a 2-beta-substituent with two hydrogen-bond acceptors. The insensitivity of the ester moiety to steric and electronic factors suggests its modification to provide site-specific irreversible ligands.

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页码：135 / 140

页数：6

相关论文

共 23 条

[1]

ABRAHAM P, IN PRESS J MED CHEM

[2]

BOJA JW, 1991, MOL PHARMACOL, V39, P339

[3] NEW, POTENT COCAINE ANALOGS - LIGAND-BINDING AND TRANSPORT STUDIES IN RAT STRIATUM [J].

BOJA, JW ;

CARROLL, FI ;

RAHMAN, MA ;

PHILIP, A ;

LEWIN, AH ;

KUHAR, MJ .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1990, 184 (2-3) :329-332

[4] [I-125] RTI-55 - A POTENT LIGAND FOR DOPAMINE TRANSPORTERS [J].

BOJA, JW ;

PATEL, A ;

CARROLL, FI ;

RAHMAN, MA ;

PHILIP, A ;

LEWIN, AH ;

KOPAJTIC, TA ;

KUHAR, MJ .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1991, 194 (01) :133-134

[5] HIGH-AFFINITY STEREOSPECIFIC BINDING OF [H-3] COCAINE IN STRIATUM AND ITS RELATIONSHIP TO THE DOPAMINE TRANSPORTER [J].

CALLIGARO, DO ;

ELDEFRAWI, ME .

MEMBRANE BIOCHEMISTRY, 1988, 7 (02) :87-106

[6]

CALLIGARO DO, 1987, J PHARMACOL EXP THER, V243, P61

[7] SYNTHESIS AND LIGAND-BINDING OF COCAINE ISOMERS AT THE COCAINE RECEPTOR [J].

CARROLL, FI ;

LEWIN, AH ;

ABRAHAM, P ;

PARHAM, K ;

BOJA, JW ;

KUHAR, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :883-886

[8] SYNTHESIS, LIGAND-BINDING, QSAR, AND COMFA STUDY OF 3-BETA-(PARA-SUBSTITUTED PHENYL)TROPANE-2-BETA-CARBOXYLIC ACID METHYL-ESTERS [J].

CARROLL, FI ;

GAO, YG ;

RAHMAN, MA ;

ABRAHAM, P ;

PARHAM, K ;

LEWIN, AH ;

BOJA, JW ;

KUHAR, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (09) :2719-2725

[9] COMPOUNDS AFFECTING CENTRAL NERVOUS-SYSTEM .4. 3BETA-PHENYLTROPANE-2-CARBOXYLIC ESTERS AND ANALOGS [J].

CLARKE, RL ;

DAUM, SJ ;

GAMBINO, AJ ;

ACETO, MD ;

PEARL, J ;

LEVITT, M ;

CUMISKEY, WR ;

BOGADO, EF .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1260-1267

[10] THE 3-DIMENSIONAL STRUCTURE OF THE COCAINES .1. COCAINE AND PSEUDOCOCAINE [J].

FINDLAY, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (11) :2855-2862