23549-24-8

Usage

Uses

Used in Pharmaceutical Industry:
(20E)-3beta-hydroxypregna-5,16-dien-20-one 20-oxime 3-acetate is used as an anti-inflammatory and immunosuppressive agent for the treatment of various inflammatory conditions such as asthma, allergic rhinitis, and autoimmune diseases. Its potent anti-inflammatory properties make it a promising candidate for the management of these conditions.
Used in Oncology Research:
(20E)-3beta-hydroxypregna-5,16-dien-20-one 20-oxime 3-acetate is used as a potential anti-tumor and anti-cancer agent. Its anti-cancer properties are being investigated for potential oncology treatments, offering a new avenue for cancer therapy.
Used in Inflammatory Bowel Disease Research:
(20E)-3beta-hydroxypregna-5,16-dien-20-one 20-oxime 3-acetate is used as a potential treatment for inflammatory bowel disease and other inflammatory disorders. Its ability to inhibit the production of pro-inflammatory cytokines makes it a promising candidate for the management of these conditions.

Upstream product

• 1045-71-2 20-hydroxyiminopregna-5,16(20)-dien-3β-ol 
• 108-24-7 acetic anhydride 
• 979-02-2 16-dehydropregnenolone acetate 
• 512-04-9 diosgenin 
• 212952-62-0 (25S)-3β,26-diacetoxy-furosta-5,20(22)-diene 

Downstream Products

• 853-23-6 prasterone acetate 
• 979-02-2 16-dehydropregnenolone acetate 
• 1045-71-2 20-hydroxyiminopregna-5,16(20)-dien-3β-ol 
• 53-43-0 dehydroepiandrosterone 
• 434-13-9 Lithocholic acid 
• 474-25-9 chenodeoxycholic acid 
• 128-13-2 ursodeoxycholic acid 
• 4651-67-6 7-Ketolithocholic acid 

Relevant academic research and scientific papers

Reactivity of steroidal 1-azadienes toward enamines: an approach to novel chiral penta- And hexacyclic steroids

The chemical behavior of steroidalN-sulfonyl-1-azadienes toward carbonyl compounds, in the presence of pyrrolidine, is described. With aldehydes, these azadienes participate in hetero-Diels-Alder reactions with thein situgenerated enamines. The stereoselectivity results from the approach of the dienophiles from the less hindered α-face of the steroid, with the pyrrolidine moietyendoand retention of the enaminetransgeometry. This diastereoselective synthetic methodology led to a new class of chiral pentacyclic steroids. Interestingly, the studied steroidal scaffolds follow a different mechanistic pathway with cyclic ketones. They undergo a diastereoselective annulation reaction, under enamine catalysis, affording chiral hexacyclic steroids.

D-Ring modification of steroids: synthesis of isoxazole annulated steroids from des D-formyl alkyne via 1,3-dipolar cycloaddition reaction

The reaction of 17,17-dichloro-androst-16(E)-chloromethylene with secondary amine base afforded substitution products of exocyclic D-ring ketones, in contrast to the reaction of alkaline base which cleaved steroidal D-ring to des-D formyl alkyne. The des-

Synthesis and evaluation of some novel pregnane derivatives as anti-hyperlipidemic and anti-oxidant agents

In the present paper, synthesis of few novel pregnane derivatives and their evaluation as potential anti-hyperlipidemic and anti-oxidant agents has been reported. The synthesis of 3β-hydroxy-16α-methoxy pregn-5-en-20-one (4) was achieved by reaction of 3β-hydroxy-5,16-pregnadiene-20-one (3) with KOH/MeOH under reflux. Compound 4 on treatment with succinic and phthalic anhydride afforded compound 6 and 7, respectively. The reaction of the C-20-oxime-pregnadiene (8) with 1,5-dibromohexane yielded 20-(O-6-bromo hexyl)-oximino-3β-hydroxy-pregn-5, 16-diene (9). A novel heterocyclic derivative 3β-hydroxy-androst-5-en [17,16-c]-2′-methyl-7′ bromo-3′,4′-dihydro quinoline (16) was synthesized by reaction of 3 with 3-bromoaniline. However, attempted synthesis of other heterocyclic derivatives by reaction of (3) with other halogenated amine led to Aza-Michael addition products (10-14). The synthesized compounds were also evaluated for their anti-hyperlipidemic and anti-oxidant activities. Compounds 6 and 14 were found to exhibit more lipid lowering and antioxidant activities in comparison to other compounds.

Synthesis of D-Ring Annulated Pyridosteroids from β-Formyl Enamides and Their Biological Evaluations

Herein, we report the synthesis of a novel class of substituted androst[17,16-b]pyridines (pyridosteroids) from the reaction of β-formyl enamides with alkynes in high yields. The optimized reaction protocol was extended to acyclic and cyclic β-formyl enamides to afford nonsteroidal pyridines. Cell survival assay of all compounds were carried against prostate cancer PC-3 cells wherein 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine showed the highest cytotoxic activity. Phase contrast microscopy and flow cytometry studies exhibited marked morphological features characteristic of apoptosis in 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine and abiraterone treated PC-3 cells. The treatment of 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine induces G2/M phase cell cycle arrest in prostate cancer PC-3 cells. Enhancement of apoptotic inductions of PC-3 cells by 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine and abiraterone through the activation of caspases-6, -7, and -8 pathways were supported by qRT-PCR. In silico study of the compound 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine showed stable and promising interaction with the key caspase proteins. Our studies revealed that the pyridosteroid 3-hydroxy-5-en-2′,3′-dicarbethoxy-androst[17,16-b]pyridine, bearing pyridine-2,3-dicarbethoxy pharmacophore, facilitated initiation of caspase-8 and activates downstream effectors caspase-6 and caspase-7 and thereby triggering apoptosis of PC-3 cancer cells.

Reactivity of Steroidal 1-Azadienes toward Carbonyl Compounds under Enamine Catalysis: Chiral Penta- and Hexacyclic Steroids

The synthesis and reactivity of a steroidal N-sulfonyl-1-azadiene, derived from 16-dehydropregnenolone acetate, toward carbonyl compounds under enamine catalysis is disclosed. An unexpected annulation reaction was observed involving an initial stereoselec

METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF

The present application relates to a method of preparing compounds of Formula (I) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof, R1 is H, α-OH, β-ΟΗ, or an oxo group.

PREGNANE-OXIMINO-AMINOALKYLETHERS AND PROCESS FOR PREPARATION THEREOF, USEFUL AS ANTIDIABETIC AND ANTIDYSLIPIDEMIC AGENTS

The present invention relates to the synthesis of pregnane-oximino-aminoalkyl-ethers and their antidiabetic and antidyslipidemic activities. More particularly, the invention relates to the synthesis of compounds of formula 3 and biological profile thereof. Further the invention relates to compounds of formula 3 and pharmaceutically acceptable salts thereof.

Expedient synthesis of some novel pregnane derivatives and their evaluation as anti-oxidant and anti-dyslipidemic agents

Synthesis of a number of novel pregnane derivatives has been described in detail. They were prepared by reaction of 3β-hydroxy-5, 16-pregnadiene-20-one (2) with diethylene glycol, 2-methoxy ethanol, 1,2-propane diol, p-chloroaniline and p-fluoroaniline, respectively. The structures of these newly synthesized compounds have been established on basis of physical, analytical and spectral data. These pregnane derivatives have been evaluated for their anti-dyslipidemic activity (Triton model) and in vitro antioxidant activities. Out of the 12 compounds tested, 3 of them showed potent anti-dyslipidemic activity and 7 showed potent antioxidant and scavenger of oxygen free radicals. Springer Science+Business Media, LLC 2010.

17-Oximino-5-androsten-3β-yl esters: Synthesis, antiproliferative activity, acute toxicity, and effect on serum androgen level

The 17-oximino-5-androsten-3β-yl esters (10a- 10j) were synthesized from commercially available (25R)- 5-Spirosten-3β-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against prostate specific cancer cell line DU-145, acute toxicity, and effect on serum androgen level and were compared with Finasteride used as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data, and biological evaluation for the synthesized compounds are reported. Springer Science+Business Media, LLC 2010.

Synthesis, antiproliferative activity, acute toxicity and assessment of the antiandrogenic activities of new androstane derivatives

A number of 17-oxo-5-androsten-3β-yl esters (9a-9f) and 3β-alkoxy-5-androsten-17-ones (11a-11e) were synthesized from commercially available (25R)-5-spirosten-3β-ol (Diosgenin) (4) as starting material. The synthesized compounds were evaluated for their antiproliferative activity against the prostate-specific cancer cell line DU-145, acute toxicity and effect on serum androgen levels, and compared with finasteride as positive control. Some of the compounds exhibited better cytotoxicity and antiandrogenic activity than the reference control. The detailed synthesis, spectroscopic data and biological activity of the synthesized compounds are reported.