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

被引：40

作者：

SCHMIDHAMMER, H ^{[1
]}

SMITH, CFC ^{[1
]}

ERLACH, D ^{[1
]}

KOCH, M ^{[1
]}

KRASSNIG, R ^{[1
]}

SCHWETZ, W ^{[1
]}

WECHNER, C ^{[1
]}

机构：

[1] RECKITT & COLMAN PLC,DIV PHARMACEUT,HULL HU8 7DS,N HUMBERSIDE,ENGLAND

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1990年 / 33卷 / 04期

关键词：

D O I：

10.1021/jm00166a018

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of cyprodime-related compounds (2, 4-12, and 26) has been synthesized and evaluated for opioid agonist and antagonist activity with the mouse vas deferens and guinea pig ileum preparations. None of the changes to cyprodime, including the introduction of a 3-OMe group, increasing and decreasing the size of or completely removing the substituent in position 4, replacing the N-cyclopropylmethyl group with an N-allyl group, or replacing the 14-OMe with a 14-OEt substituent, resulted in an improved μ antagonist profile and most were detrimental either in terms of μ selectivity and potency or increased agonist activity. Increasing the length of the substituent in position 4 resulted in a compound (6a) with a very similar profile to that of cyprodime. © 1990, American Chemical Society. All rights reserved.

引用

页码：1200 / 1206

页数：7

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