Joyce M J, Hiremath S V, Mattammal M B, Elliott W H
Steroids. 1984 Jul;44(1):95-101. doi: 10.1016/s0039-128x(84)80020-3.
Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-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-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.
制备了7α-羟基-4-胆甾烯-3-酮的类似物，以确定肝微粒体12α-类固醇羟化酶最大活性所需的结构特征。将源自鹅去氧胆酸的3α,7α-二羟基-5β-胆烷-24-羧酸甲酯用碳酸银/硅藻土在C-3位氧化。产物经水解并用二氧化硒脱氢，得到3-氧代-7α-羟基-4-胆烯-24-羧酸。5β-胆甾烷-3α,7α,25-三醇和5β-胆甾烷-3α,7α,12α,25-四醇同样在C-3位氧化并脱氢，分别得到7α,25-二羟基-4-胆甾烯-3-酮和7α,12α,25-三羟基-4-胆甾烯-3-酮。产物通过薄层色谱和气相色谱、紫外、红外、质子共振和质谱进行表征。
