2063-90-3

Upstream product

• 67-56-1 methanol 
• 1508-94-7 3,5-seco-4-nor-cholestan-5-one-3-oic acid 
• 186581-53-3 diazomethane 
• 57-88-5 cholesterol 
• 601-57-0 Cholest-4-en-3-one 

Relevant academic research and scientific papers

Synthesis, biological evaluation and in silico studies of novel 5-aza-bhomo- 3,5-secosteroids as potential 5α-reductase inhibitors

Benign prostatic hyperplasia is non-malignant enlargement of prostate gland which results in severe lower urinary tract symptoms and affects the quality of life of patients. 5α-Reductase inhibitors play a crucial role in the management of benign prostatic diseases with low toxicity and have been a major thrust area for its application in prostate cancers with limited success. In continuation of our program to develop novel 5α-reductase inhibitors, we report herein the synthesis and biological evaluation of 5a-oxo-5-aza-B-homo-3,5-seco-4-nor-cholestan-3-oic acid and 25(R)-5a-oxo-5-aza- B-homo-3,5-seco-4-nor-spirostan-3-oic acid derivatives. In vitro evaluation using human embryonic kidney cell line (HEK) based assay revealed compound MK-234 as most potent inhibitor with an IC50 value of 0.474 ±0.041 μM followed by MK-233 with an IC50 value 4.84 ± 0.088 μM as compared to clinically used drug finasteride (IC50 = 30.3 nM). Compound MK-235 and MK-236 also exhibited moderate inhibition with an IC50 value of 9.24 ± 0.796 and 13.148 ± 0.379 μM, respectively. Additionally, in silico ADME predictive studies were also carried out to assess the 'druggability properties' of the synthesised compounds.

USE OF 3,5-SECO-4-NOR-CHOLESTANE DERIVATIVES FOR OBTAINING A CYTOPROTECTIVE DRUG

The present invention relates to the use of 3,5-seco-4-nor-cholestane derivatives for obtaining a cytoprotective drug, with the exception of a neuroprotective drug, notably a cardioprotective or hepatoprotective drug.

Novel Derivatives of 3.5-Seco-4-Norcholestane and Use Thereof

The invention relates to compounds of formula (I): where X+Y=keto, or X=OH and Y=H, or X+Y=oxime or methyloxime, B=OH and C+D=H, or C+D=C1-C4 linear or branched alkyl, or C=H and D=C1-C4 linear or branched alkyl, or B+C=keto and D=methyl, hydroxyl, or methylamino, or B and C=H and D=methylamino, or B+C=oxime and D=methyl and R=C1-C10 linear or branched alkyl, the salts, esters, or salts of esters thereof as medicament, in particular as neuroprotectors, novel compounds of formula (I) and pharmaceutical compositions.

Thermolysis and photolysis of two steroidal hydroxamic acid methanesulfonates

Thermolysis or photolysis of N-methanesulfonyloxy-4-aza-5α-cholestan- 3-one gave derivatives of 4-azacholestan-3-one, 4-aza-A-nor-B-homocholestan- 3-one, 3-aza-A-norcholestane, bis (4-aza-3-oxocholest-5-en-6-yl) methane, and bis(3-aza-A-norcholestan-3-yl) urea. The corresponding 5β-methanesulfonate gave the 5β (coprostane) analogues. Evidence for the mechanism of formation of these products, including a Favorski-like ring contraction and amide oxidation by methanesulfonic acid, is presented. Detailed 1H and 13C assignments are made for many of the products, and ultraviolet absorption for seven steroidal enamides is tabled. Long-range homo- and heteronuclear NMR connectivities were used to confirm the structure of three dimeric compounds and to assign the configuration of the methoxy function of 4-aza-5-methoxy- A-nor-β-homocholestan-3-one to be 5α. Thermolysis or photolysis of N-methanesulfonyloxy-4-aza-5α-cholestan-3-one gave derivatives of 4-azacholestan-3-one, 4-aza-A-nor-B-homocholestan-3-one, 3-aza-A-norcholestane, bis (4-aza-3-oxocholest-5-en-6-yl) methane, and bis(3-aza-A-norcholestan-3-yl) urea. The corresponding 5β-methanesulfonate gave the 5β (coprostane) analogues. Evidence for the mechanism of formation of these products, including a Favorski-like ring contraction and amide oxidation by methanesulfonic acid, is presented. Detailed 1H and 13C assignments are made for many of the products, and ultraviolet absorption for seven steroidal enamides is tabled. Long-range homo- and heteronuclear NMR connectivities were used to confirm the structure of three dimeric compounds and to assign the configuration of the methoxy function of 4-aza-5-methoxy-A-nor-β-homocholestan-3-one to be 5α.

Metabolism in porifera VI. Role of the 5,6 double bond and the fate of the C-4 of cholesterol during the conversion into 3 β-hydroxymethyl-A-nor-5 α-steranes in the sponge Axinella verrucosa

During the conversion of cholesterol into 3 β-hydroxymethyl-A-nor-5 α-cholestane by the sponge Axinella verrucosa, the carbon-3 of this latter originate from carbon-4 of cholesterol. Cholestanol moreover does not seem an intermediate in this conversion.