PALLADIUM-CATALYZED SYNTHESIS OF C3-SUBSTITUTED 3-DEOXYMORPHINES

被引：16

作者：

HEDBERG, MH

JOHANSSON, AM

FOWLER, CJ

TERENIUS, L

HACKSELL, U

机构：

[1] UNIV UPPSALA, UPPSALA BIOMED CTR, S-75123 UPPSALA, SWEDEN

[2] ASTRA PAIN CONTROL AB, PRECLIN RES & DEV, NOVUM UNIT, S-14157 HUDDINGE, SWEDEN

[3] KAROLINSKA INST, DEPT DRUG DEPENDENCE RES, S-17176 STOCKHOLM, SWEDEN

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1994年 / 4卷 / 21期

关键词：

D O I：

10.1016/S0960-894X(01)80277-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The facile synthesis of a series of C3-substituted analogues of 3-deoxymorphine (2) by use of palladium-catalyzed reactions is described. Although none of the new compounds were as potent as morphine at either kappa-, mu- or delta-opioid receptors, the mu-receptor selectivity of the C3-furyl derivative 7 approached that of morphine.

引用

收藏

页码：2527 / 2532

页数：6

相关论文

共 18 条

[1] 175 YEARS OF ISOQUINOLINE DRUGS [J].

BROSSI, A .

HETEROCYCLES, 1978, 11 :521-547

[2] SEARCH FOR A BETTER ANALGESIC [J].

EDDY, NB ;

MAY, EL .

SCIENCE, 1973, 181 (4098) :407-414

[3]

EVANS SM, 1990, ANNU REP MED CHEM, V25, P11

[4] CONNECTIONS TO THE DIRECTED ORTHO METALATION STRATEGY - PD(0)-CATALYZED CROSS COUPLING OF ARYL BORONIC ACIDS WITH ARYL TRIFLATES [J].

FU, JM ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1990, 31 (12) :1665-1668

[5] FACILE SYNTHESES OF APORPHINE DERIVATIVES [J].

HEDBERG, MH ;

JOHANSSON, AM ;

HACKSELL, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (11) :845-846

[6]

HITE GJ, 1989, PRINCIPLES MED CHEM, P239

[7] SYNTHESIS OF DIARYLIC COMPOUNDS BY PALLADIUM CATALYZED REACTION OF AROMATIC TRIFLATES WITH BORONIC ACIDS [J].

HUTH, A ;

BEETZ, I ;

SCHUMANN, I .

TETRAHEDRON, 1989, 45 (21) :6679-6682

[8] O-3-(2-CARBOMETHOXYALLYL) ETHERS OF OPIOID LIGANDS DERIVED FROM OXYMORPHONE, NALTREXONE, ETORPHINE, DIPRENORPHINE, NORBINALTORPHIMINE, AND NALTRINDOLE - UNEXPECTED O-3-DEALKYLATION IN THE OPIOID RADIOLIGAND DISPLACEMENT ASSAY [J].

KLEIN, P ;

NELSON, WL .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) :4589-4594

[9] PALLADIUM-CATALYZED COUPLING REACTIONS OF (ALPHA-ETHOXYVINYL)TRIMETHYLSTANNANE WITH VINYL AND ARYL TRIFLATES [J].

KWON, HB ;

MCKEE, BH ;

STILLE, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3114-3118

[10] [H-3]U-69593 A HIGHLY SELECTIVE LIGAND FOR THE OPIOID K-RECEPTOR [J].

LAHTI, RA ;

MICKELSON, MM ;

MCCALL, JM ;

VONVOIGTLANDER, PF .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1985, 109 (02) :281-284