Synthesis and biological evaluation of 14-alkoxymorphinans.: 16.: 14-O-alkyl derivatives of the μ opioid receptor antagonist cyprodime

被引：10

作者：

Schmidhammer, H

Krassnig, R

Greiner, E

Traynor, JR

机构：

[1] Univ Innsbruck, Inst Pharmaceut Chem, A-6020 Innsbruck, Austria

[2] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

HETEROCYCLES | 1998年 / 49卷

关键词：

D O I：

10.3987/COM-98-S60

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 14-O-benzyl derivatives of cyprodime and 3-hydroxycyprodime (compounds (5) and (6), respectively) were synthesized in several steps from 3-desoxynaltrexone (2a) and naltrexone (2), respectively. In the mouse vas deferens preparation it was found that a 14-O-benzyl group could enhance mu opioid receptor affinity in cyprodime while the mu affinity of 3-hydroxycyprodime was not changed.

引用

收藏

页码：489 / 497

页数：9

相关论文

共 9 条

[1]

KRASSNIG R, 1994, HETEROCYCLES, V38, P877

[2] TRITIUM LABELING OF CYPRODIME (=(-)-17-(CYCLOPROPYLMETHYL)-4,14-DIMETHOXYMORPHINAN-6-ONE), A MU-RECEPTOR-SELECTIVE OPIOID ANTAGONIST [J].

OTVOS, F ;

TOTH, G ;

SCHMIDHAMMER, H .

HELVETICA CHIMICA ACTA, 1992, 75 (05) :1718-1720

[3] AN APPROACH TO THE DESIGN OF RECEPTOR-TYPE-SELECTIVE NONPEPTIDE ANTAGONISTS OF PEPTIDERGIC RECEPTORS - DELTA OPIOID ANTAGONISTS [J].

PORTOGHESE, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1757-1762

[4] SYNTHESIS AND BIOLOGICAL EVALUATION OF 14-ALKOXYMORPHINANS .11. 3-HYDROXYCYPRODIME AND ANALOGS - OPIOID ANTAGONIST PROFILE IN COMPARISON TO CYPRODIME [J].

SCHMIDHAMMER, H ;

JENNEWEIN, HK ;

KRASSNIG, R ;

TRAYNOR, JR ;

PATEL, D ;

BELL, K ;

FROSCHAUER, G ;

MATTERSBERGER, K ;

JACHSEWINGER, C ;

JURA, P ;

FRASER, GL ;

KALININ, VN .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (16) :3071-3077

[5] SYNTHESIS AND BIOLOGICAL EVALUATION OF 14-ALKOXYMORPHINANS .3. EXTENSIVE STUDY ON CYPRODIME-RELATED COMPOUNDS [J].

SCHMIDHAMMER, H ;

SMITH, CFC ;

ERLACH, D ;

KOCH, M ;

KRASSNIG, R ;

SCHWETZ, W ;

WECHNER, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (04) :1200-1206

[6] Synthesis and biological evaluation of 14-alkoxymorphinans -: Part 15 -: Novel δ opioid receptor antagonists with high affinity and selectivity in the 14-alkoxy-substituted indolomorphinan series [J].

Schmidhammer, H ;

Krassnig, R ;

Greiner, E ;

Schütz, J ;

White, A ;

Berzetei-Gurske, IP .

HELVETICA CHIMICA ACTA, 1998, 81 (06) :1064-1069

[7] SYNTHESIS AND BIOLOGICAL EVALUATION OF 14-ALKOXYMORPHINANS .2. (-)-N-(CYCLOPROPYLMETHYL)-4,14-DIMETHOXYMORPHINAN-6-ONE, A SELECTIVE MU-OPIOID RECEPTOR ANTAGONIST [J].

SCHMIDHAMMER, H ;

BURKARD, WP ;

EGGSTEINAEPPLI, L ;

SMITH, CFC .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :418-421

[8]

SCHMIDHAMMER H, 1993, CURR TOP MED CHEM, V1, P261

[9]

SCHMIDHAMMER H, 1998, IN PRESS PROGR MED C, V35