N-（甲磺酰基）-16-苯氧基前列腺素羧酰胺：组织选择性子宫兴奋剂。

N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.

作者信息

Schaaf T K, Bindra J S, Eggler J F, Plattner J J, Nelson A J, Johnson M R, Constantine J W, Hess H J, Elger W

出版信息

J Med Chem. 1981 Nov;24(11):1353-9. doi: 10.1021/jm00143a018.

Abstract

In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

摘要

为了开发对天然物质代谢失活途径具有抗性的组织选择性前列腺素类似物，合成了在C-1位用磺酰亚胺部分修饰且在正戊基甲醇侧链用取代苯氧基修饰的杂合化合物，并在多种体外模型中进行了评估。其中几种类似物表现出强效、组织选择性的子宫刺激活性，这一发现随后在对该系列中的一个成员N-(甲磺酰基)-16-苯氧基-ω-四去甲-PGE2-羧酰胺（CP-34089/ZK-57671，舒前列素）的临床研究中得到证实。