一系列N-未取代氨基磺酸酯类化合物的雄性抗生育特性的合成与评价

Synthesis and evaluation of the male antifertility properties of a series of N-unsubstituted sulfamates.

作者信息

Hirsch A F, Kasulanis C, Kraft L, Mallory R A, Powell G, Wong B

出版信息

J Med Chem. 1981 Jul;24(7):901-3. doi: 10.1021/jm00139a029.

Abstract

A series of six aliphatic and one carbocyclic N-unsubstituted sulfamates have been synthesized and evaluated as potential male antifertility agents. Three of the aliphatic sulfamates, 1,2-ethanediyl sulfamate (1), 1,3-propanediyl sulfamate (2), and 1,4-butanediyl sulfamate (3), when administered orally to male rats caused a decrease in the number of pregnant females and/or implantation coupled with increased embryonic and fetal resorption. The compounds were prepared by treating the appropriate glycol salt with sulfamoyl chloride or by the cleavage of a tert-butylsulfamate with trifluoroacetic acid.

摘要

已合成了一系列六种脂肪族和一种碳环的 N-未取代氨基磺酸酯，并将其作为潜在的男性抗生育剂进行了评估。三种脂肪族氨基磺酸酯，即 1,2-乙二基氨基磺酸酯（1）、1,3-丙二基氨基磺酸酯（2）和 1,4-丁二基氨基磺酸酯（3），口服给予雄性大鼠后，导致怀孕雌性大鼠数量减少和/或着床减少，同时胚胎和胎儿吸收增加。这些化合物是通过用磺酰氯处理适当的二醇盐或用三氟乙酸裂解叔丁基氨基磺酸酯来制备的。