17597-24-9

Usage

Uses

Used in Pharmaceutical Industry:
(4beta,5beta)-4,5-epoxypregnane-3,20-dione is used as a key intermediate in the synthesis of corticosteroids for its important biological and pharmacological activities.
Used in Anti-inflammatory and Immunosuppressive Applications:
(4beta,5beta)-4,5-epoxypregnane-3,20-dione is used as an anti-inflammatory and immunosuppressive agent due to its potential to modulate the immune system and reduce inflammation.
Used in Treatment of Inflammatory and Autoimmune Diseases:
(4beta,5beta)-4,5-epoxypregnane-3,20-dione may have potential applications in the treatment of various inflammatory and autoimmune diseases, given its unique chemical structure and pharmacological properties.
Used in Research and Development:
(4beta,5beta)-4,5-epoxypregnane-3,20-dione is a molecule of interest for further research and development in the field of medicine, particularly for its potential applications in treating various diseases and improving existing treatments.

Upstream product

• 57-83-0 Progesterone 

Downstream Products

• 1164-81-4 4-Chloro-pregn-4-ene-3,20-dione 
• 57-83-0 progesterone 
• 650-66-8 4-Hydroxy-pregnen-(4)-dion-(3,20) 

Relevant academic research and scientific papers

RUTHENIUM COMPLEX AND PRODUCTION METHOD THEREOF, CATALYST, AND PRODUCTION METHOD OF OXYGEN-CONTAINING COMPOUND

PROBLEM TO BE SOLVED: To provide a ruthenium complex that is particularly useful as a catalyst for oxidizing a substrate having a carbon-hydrogen bond. SOLUTION: The ruthenium complex represented by the general formula (i) or a cis conformer thereof is provided. In the general formula (i), R1 represents H, a phenyl group or a substituted phenyl group; R2 represents H, a phenyl group or an alkyl group; L1 represents halogen or water molecule; L2 represents triphenylphosphine, pyridine, imidazole or dimethylsulfoxide; X represents halogen; and n represents 1 or 2. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

Unambiguous assignment of 13C NMR signals in epimeric 4,5-epoxy-3-oxo-steroids assisted by X-ray diffraction and Gauge Invariant Atomic Orbitals calculation of absolute isotropic shieldings

Complete assignments of the 13C signals of diastereomeric 4,5-epoxy-3-oxo steroids based on a combination of 1D and 2D NMR techniques are described The assignments were corroborated or corrected by calculation of the absolute isotropic 13C NMR shieldings using the Gauge Invariant Atomic Orbitals (GIAO) method at B3LYP/6-31+G(d,p) level. ARKAT-USA, Inc.

Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives

Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a-g and 10a-g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure-activity relationship was discussed.

Synthesis and cytotoxicity of some novel 21E-benzylidene steroidal derivatives

A series of novel derivatives of 21E-benzylidene-pregn-1,4-diene-3,20-dione 7a-g and 21E-benzylidene-4-chloro-pregn-1,4-diene-3,20-dione 8a-g was synthesized from the commercially available progesterone. These title compounds were evaluated for their cyto

Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate

Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations of steroids are reported. Among them, highly stereoselective epoxidation of Δ5-B-nor-cholestanes was achieved. Moreover, the method is chemoselective for the 5,6-position and can be applied to the epoxidation of ring-A enones.

Diastereoselective epoxidation of olefins by organo sulfonic peracids, II

We have investigated the behaviour of sulfonic peracids 2 in situ generated towards olefins 7a, 7b, 9, 11, 14, 16, 18, allylic acid and homoallylic alcohols 20, 22, 24, 26, 28, 30, 33 and α,β-unsaturated ketones 35, 37, 39. Generally, the epoxidation proceeds in a peracid-like manner with greater diastereoselectivity than those by common oxidants. In particular, the epoxidation of Δ4 3-ketosteroids 39a-i led to 4α,5α-epoxides 40a-i with remarkable high de-values. Enhanced α-selectivity was also found in the epoxidation of cholesterol 28b. Due to the mild reaction conditions, even acid sensitive epoxides 8a, 8b, 10, 12, 13, 15, 17, 19 were obtained in good yields.

New Routes to 4-Substituted Steroids: Synthesis of 4-Cyanoprogesterone, a Potent Inhibitor of the Enzyme 5&α-Reductase

Two new synthetic route to 4-substituted derivatives of progesterone are described: one involves the palladium-catalysed addition of alkenes to 4-(trifluoromethanesulfonyloxy)progesterone, and the other involves the addition of the anion of acetonitrile t

Peroxide oxidation of Δ4-3-ketosteroids

Treatment of Δ4-3-ketosteroids with tert-butyl hydroperoxide in the presence of lithium hydroxide leads to the formation of the corresponding 4β,5β epoxides stereospecifically and in good yield.The stereospecificity of this reaction is explicable in terms of the accepted mechanism for the hydrogen peroxide epoxidation of Δ4-3-ketosteroids.The use of aqueous sodium peroxide as oxidant leads to the production of the corresponding Δ4-3,6-diones.A mechanism for this reaction is proposed in which the key step is autooxidation of the corresponding deconjugated Δ5-3-ketone, produced from the starting material in situ by the action of the reagents.Lithium peroxide does not oxidize androst-4-ene-3,17-dione at C-6, but produces the 4,5-epoxides in low yield together with an A-nor-3,5-secoacid.