Abstract
A new class of 3α-ester derivatives of pregnenolone, using Mitsunobu reaction conditions, is described. The scheme involved the conversion of pregnenolone (4) into 20-(2-hydroxyethyl)imino-pregn-5-en-3β-ol (8), followed by tritylation to give the analogue 9. Treatment of 9 with various aryl carboxylic acids afforded the tritylated 3α-ester pregnenolone analogues 18–23. Detritylation with AcOH furnished the 3α‐substituted aryl ester derivatives 24–29. Analogously, the 3β-ester analogues 31 and 32 were synthesized from pregnenolone (4) and its analogue 30, using Steglich coupling method, by treatment with rhodamine B in the presence of DCC/DMAP. These derivatives were screened for their CYP17α hydroxylase inhibition activity expressed in Escherichia coli. Compound 27 was the most active inhibitor among both series, with IC50 value of 1.12 μM and selectivity profile of 88.56 % inhibition of CYP17α hydroxylase enzyme.
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