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  • Title: Synthesis of regioisomeric 17beta-N-phenylpyrazolyl steroid derivatives and their inhibitory effect on 17alpha-hydroxylase/C(17,20)-lyase.
    Author: Iványi Z, Wölfling J, Görbe T, Szécsi M, Wittmann T, Schneider G.
    Journal: Steroids; 2010 Jun; 75(6):450-6. PubMed ID: 20206195.
    Abstract:
    The reaction of 3beta-hydroxy-21-hydroxymethylidenepregn-5-en-3beta-ol-20-one (1) with phenylhydrazine (2a) affords two regioisomers, 17beta-(1-phenyl-3-pyrazolyl)androst-3-en-3beta-ol (5a) and 17beta-(1-phenyl-5-pyrazolyl)androst-5-en-3beta-ol (6a). The direction of the ring-closure reactions of 1 with p-substituted phenylhydrazines (2b-e) depends strongly on the electronic features of the substituents. Oppenauer oxidation of 3beta-hydroxy-17beta-exo-heterocyclic steroids 5a-e and 6a-e yielded the corresponding Delta(4)-3-ketosteroids 9a-e and 10a-e. The inhibitory effects (IC(50)) of these compounds on rat testicular C(17,20)-lyase were investigated by means of an in vitro radioligand incubation technique.
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