Collect. Czech. Chem. Commun. 2009, 74, 643-650
Published online 2009-04-06 11:33:36

Preparation of steroid sulfamates and their interaction with GABAA receptor

Vojtěch Kapras, Eva Šťastná, Hana Chodounská*, Vladimír Pouzar and Zdena Krištofíková

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., CZ-166 10 Prague 6, Czech Republic


Sulfamoyl chloride was used for the preparation of 3α- and 3β-sulfamates of steroids: 20-oxo-5α-pregnan-3α-yl sulfamate (4), 20-oxo-5α-pregnan-3β-yl sulfamate (5), 20-oxo-5β-pregnan-3α-yl sulfamate (7), and 20-oxo-5β-pregnan-3β-yl sulfamate (9) from the corresponding 3α- and 3β-alcohols. Sulfur trioxide–pyridine complex was employed for the preparation of 20-oxo-5α-pregnan-3α-yl pyridinium sulfate (10). The specific steroid binding was detected by the decrease of the specific [35S]-tert-butylbicyclo[2.2.2]phosphorothionate binding after application of the tested compounds.

Keywords: Sulfamates; Neurosteroids; GABAA receptors; Pregnane.

References: 14 live references.