Biomedical subjects
A F Hirsch
Publications and source records attributed to A F Hirsch.
Synthesis and evaluation of the male antifertility properties of a series of N-unsubstituted sulfamates.
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.
The synthesis of 17-substituted 2alpha-chloro-5alpha-androstan-3-ols.
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Contragestational agents. 1. Steroidal O-aryloximes.
The preparation of a series of O-aryloximes of various steroids by two different routes is described. These compounds were prepared by reacting a keto steroid with a substituted O-arylhydroxylamine in the presence of an acid catalyst or, alternatively, by the reaction of a steroidal oxime with a substituted aryl halide in the presence of a suitable base. These compounds were examined for their ability to interrupt postimplantive gestation in female rats. The most significant contragestational activity was seen with compounds in which the basic steroid structure was a 5alpha-androstane and the 3-oxime was of the p-nitrophenyl series. One of the most active compounds in the series (16) was shown to have the ability to terminate pregnancy, when orally administered to rats at 2.5 mg/kg on days 9-12 of gestation. This compound was found to be devoid of androgenic activity at this dose level.
Antifertility effects of chlorine-substituted dioxolanes, dithiolanes, and dithianes in male rats.
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Blockage of fertilization in Rana pipiens by trypsin inhibitors.
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Synthesis of 21-hydroxymethylprogesterone.
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