1508-94-7

Upstream product

• 67-66-3 chloroform 
• 601-57-0 Cholest-4-en-3-one 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 71-43-2 benzene 
• 57-88-5 cholesterol 
• 1975-34-4 4β,5-epoxy-5β-cholest-3-one 
• 35878-83-2 A-nor-cholest-3-ene 

Downstream Products

• 126001-07-8 4-(2'-Methoxyphenyl)-4-aza-Δ⁵-cholesten-3-one 
• 2063-90-3 3,5-seco-4-nor-cholestane-5-one-3-methyl ester 
• 38819-47-5 3,3-diphenyl-3,5-seco-A-nor-cholest-2-en-5-one 
• 6242-19-9 (3R,3aR,5aS,6R,7R,9aS,9bS)-3-((R)-1,5-Dimethyl-hexyl)-6-(3-hydroxy-propyl)-3a,6-dimethyl-dodecahydro-cyclopenta[a]naphthalen-7-ol 
• 125132-23-2 4-(2'-Methylphenyl)-4-aza-Δ⁵-cholesten-3-one 
• 125132-24-3 4-(2',6'-Dimethylphenyl)-4-aza-Δ⁵-cholesten-3-one 
• 20237-51-8 4-benzyl-4-aza-Δ⁵-cholesten-3-one 
• 20237-53-0 4-Phenyl-4-aza-Δ⁵-cholesten-3-one 
• 2061-74-7 4-oxa-5α-cholestan-3-one 
• 5260-58-2 4-oxa-5β-cholestan-3-one 
• 38819-46-4 5,5-ethanediyldioxy-3,3-diphenyl-3,5-seco-A-nor-cholestan-3-ol 
• 2061-75-8 4-oxa-5-cholesten-3-one 

Relevant academic research and scientific papers

Beyond Pseudo-natural Products: Sequential Ugi/Pictet-Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase-Independent Death in HepG2 Cells

In this work, we describe how stereochemically complex polycyclic compounds can be generated by applying a synthetic sequence comprising an intramolecular Ugi reaction followed by a Pictet-Spengler cyclization on steroid-derived scaffolds. The resulting compounds, which combine a fragment derived from a natural product and a scaffold not found in nature. are both structurally distinct and globally similar to natural products at the same time, and interrogate an alternative region of the chemical space. One of the new compounds showed significant antiproliferative activity on HepG2 cells through a caspase-independent cell-death mechanism, an appealing feature when new antitumor compounds are searched.

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.

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.

A microwave promoted and Lewis acid catalysed solventless approach to 4-azasteroids

The preparation of 3-oxo-4-azasteroid from A-nor-3,5-secosteroid-3-oic acid is described in a solventless condition catalysed by Lewis acid under microwave irradiation. We utilized urea as an environmentally benign source for the generation of ammonia for the aza cyclization reaction.

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.

Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles

Cholesterol, testosterone acetate and dehydroepiandrosterone acetate were used as starting materials for the preparation of azasteroidal [3,2-c]- and [17,16-c]pyrazole derivatives. In case of the 4-aza androstane series, a mixture of 5α/5β epimers 8 was obtained, which were separated by chemical methods. The compounds 4, 5, 10, 12, 13, 15, 16 and 18-22 were screened for antiinflammatory activity using the carrageenan rat paw oedema model. Oxirane 22 was found to be around ten times more potent than hydrocortisone. Evaluation of compounds 14, 18 and 19 for their antineoplastic activity was also carried out at the National Cancer Institute, Bethesda, MD, USA, using standard procedures.

INTRAMOLECULAR CYCLIZATION OF STEROIDAL DIKETO ALDEHYDES TO ACETALS

As an attempt to prepare diketo aldehydes I and II conjugated ketones III and IV were converted to the respective keto diols V and VI, which were treated with periodic acid and independently with lead tetraacetate.However, instead of desired diketo aldehy

Perbenzoic Acid Oxidation of Some 3-Ketosteroids

Oxidation of 4-chlorocholest-4-en-3-one (I) with perbenzoic acid givens methyl 4-oxa-3-oxo-4-nor-5β-cholestan-5-carboxylate (IV), 3,6-dioxo-5-hydroxy-5α-cholestan-4α-yl chloride (V), 3-oxo-4-oxa-A-homo-1,4a-cholestandien-4-yl chloride (VI) and 3,4-secocholestan-2-methyl carboxy-5β-oyl chloride (VII).The 4-bromo analogue (II) of I on similar treatment provides 4a-bromo-3-oxa-A-homocholest-4a-en-4-one (VIII) and 3,4-seco-5α-cholestan-3,4-dioic acid 3-methyl ester (IX). 4β,5-Epoxy-5β-cholestan-3-one (III) under similar conditions gives 3-oxa-4aξ,5ξ-epoxy-A-homocholestane-4,6-dione (X), 4-oxa-4-nor-5-formyloxy-5α-cholestan-3-one (XI) and 5-oxo-3,5-seco-4-norcholestan-3-oic acid (XII).The structures of these products have been established by their analytical and spectral data.

A CONVENIENT PROCEDURE FOR PREPARATIVE SCALE OXIDATION OF ENONES

A convenient procedures for oxidative cleavage of cyclic enones on a preparative scale is described.