17974-77-5Relevant articles and documents
Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption
Offei, Samuel D.,Arman, Hadi D.,Yoshimoto, Francis K.
, (2019)
7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3-desoxy-Δ4-7α-formate steroid precursor to form 7α-formyloxy-cholest-4-en-3-one, which was saponified to yield 7α-hydroxy-cholest-4-en-3-one.
Selective reduction of α,β-unsaturated steroidal carbonyl compounds by NaBH4in presence of guanidine hydrochloride in dioxane
Khan, Salman Ahmad,Asiri, Abdullah M.
, p. 6331 - 6334 (2014)
A selective hydrogenation of α,β-unsaturated steroidal carbonyl compounds with NaBH4in the presence of guanidine hydrochloride in dioxane in good to excellent yields are described.
Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol
Lam, Ying-Pong,Yeung, Ying-Yeung
supporting information, p. 2369 - 2372 (2018/04/19)
A mild, efficient and organocatalytic allylic oxidation of steroids using a TBAI/TBHP protocol has been developed. A range of bioactive Δ5-en-7-ones can be easily prepared from the corresponding Δ5-steroids. The methodology features several advantages, including readily available starting materials, environmentally benign oxidant, high functional group compatibility, and metal-free catalysis.
Oxysterols: Synthesis and anti-leishmanial activities
Ghosh, Pranab,Ghosh, Ashim,Mandal, Amitava,Sultana, Sirin Salma,Dey, Somaditya,Pal, Chiranjib
, p. 65 - 73 (2016/03/04)
Oxygenated sterols (2-16) were synthesized by skeletal rearrangement of steroidal allylic alcohols. All the derivatives were screened for their anti-leishmanial activities. Compounds 3, 11 and 12 showed potent activities. Compound 12 was found least toxic and induced highest nitric oxide (NO) at 48 h. Least toxicity of compound 12 on splenocytes validated its best anti-amastigote effect and induction of NO.
