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首页> 外文期刊>Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences >Synthesis of morphan derivatives with additional substituents in 8-position
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Synthesis of morphan derivatives with additional substituents in 8-position

机译：在8位上合成带有其他取代基的吗啡衍生物

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摘要

The morphan system (2-azabicyclo[3.3.1]no-nane) as a substructure of morphine is of major interest in medicinal chemistry. Herein, the synthesis of morphan derivatives with additional substituents at the propano bridge is reported. In order to avoid the isolation of the smelly and volatile nitrile 6 and the very polar primary amine 9, an efficient one-pot, three-step sequential transformation of the mesylate 5 into amides 10 was developed. The key step of the synthesis was the stereoselective intramolecular opening of the epoxides 11a-d leading to the exo-configured 8-hydroxymorphans 12a-d. The configuration of the exo-configured hydroxymorphan 12d bearing the kappa- and sigma-pharmacophoric 3,4-dichlorophenylacetyl moiety was inverted by oxidation and stereoselective reduction. An X-ray crystal structure analysis of the benzamide 12c confirmed the relative configuration of the hydroxymorphans 12a-d and 14d.
机译：作为吗啡子结构的吗啡系统（2-氮杂双环[3.3.1]无-烷）是药物化学中的主要兴趣。在此，报道了在丙烷桥上具有另外的取代基的吗啉衍生物的合成。为了避免臭味和挥发性腈6和极性极强的伯胺9的分离，开发了甲磺酸盐5到酰胺10的有效的一锅三步顺序转化。合成的关键步骤是环氧化物11a-d的立体选择性分子内开放，导致外构型的8-羟基吗啡喃12a-d。通过氧化和立体选择性还原使带有κ-和σ-药效的3，4-二氯苯基乙酰基部分的exo-构型羟基吗啉12d的构型反转。苯甲酰胺12c的X射线晶体结构分析证实了羟基吗啡烷12a-d和14d的相对构型。

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