Bile acids. LXXIII. Synthesis of analogs of 7α-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12α-hydroxylase

Article abstract of DOI:10.1016/S0039-128X(84)80020-3

Analogs of 7α-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12α-steroid hydroxylase.Methyl 3α,7α-dihydroxy-5β-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite.The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7α-hydroxy-4-cholene-24-carboxylic acid. 5β-Cholestane-3α,7α,25-triol and 5β-cholestane-3α,7α,12α,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7α,25-dihydroxy-4-cholesten-3-one and 7α,12α,25-trihydroxy-4-cholesten-3-one, respectively.The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.