2193-00-2

Usage

Uses

Used in Pharmaceutical Industry:
5alpha,6alpha-epoxy-3beta-hydroxypregnan-20-one is used as a key intermediate in the synthesis of neuroactive steroids for the development of treatments targeting neurological and psychiatric disorders. Its role in the conversion of progesterone to allopregnanolone, a compound with anxiolytic and sedative properties, makes it a valuable component in the creation of pharmaceuticals aimed at addressing anxiety, depression, and epilepsy.
Used in Neurological Research:
5alpha,6alpha-epoxy-3beta-hydroxypregnan-20-one is used as a research compound to study its effects on neurotransmitter receptors, such as GABA receptors, and its potential involvement in neurological and psychiatric disorders. This research helps in understanding the underlying mechanisms of these disorders and contributes to the development of novel therapeutic approaches.
Used in Drug Development:
5alpha,6alpha-epoxy-3beta-hydroxypregnan-20-one is used as a target for drug development, as its modulation of neurotransmitter receptor activity and its implications in various neurological and psychiatric disorders suggest its potential as a therapeutic agent. Further research into its functions and pharmacological effects may lead to the discovery of new drugs for the treatment of depression, anxiety, and epilepsy.

Upstream product

• 108-05-4 vinyl acetate 
• 145-13-1 Pregnenolone 

Downstream Products

• 4660-45-1 6β-fluoro-5-hydroxy-5α-pregnane-3,20-dione 
• 604-20-6 6alpha-Hydroxyprogesterone 
• 2300-03-0 6α-Fluoro-4-pregnene-3,20-dione 
• 903-71-9 6α-methyl-pregn-4-ene-3,20-dione 
• 1868-98-0 6β-fluoro-3β,5-dihydroxy-5α-pregnan-20-one 
• 14148-09-5 5α,6α-epoxy-20-oxopregnan-3β-yl acetate 

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

Chemoselective epoxidation of cholesterol derivatives on a surface-designed molecularly imprinted Ru-porphyrin catalyst

A new molecularly imprinted Ru-porphyrin complex catalyst on a SiO2 support was designed, prepared, and characterized in a step-by-step manner for the C5C6 epoxidation of cholesterol derivatives. High chemoselectivity for the C5C6 epoxidation of cholesterol derivatives without protecting the 3-position OH group and other oxidizable functional groups was achieved on the molecularly imprinted catalyst.

Synthesis and biological evaluation of heterocyclic analogues of pregnenolone as novel anti-osteoporotic agents

The structural modifications of pregnenolone have been described via the introduction of heterocyclic moieties at C-17 position by limiting the acyl group. Novel heterocyclic analogues of pregnenolone have been synthesized by using Friedlander and Claisen-Schmidt reactions, and the synthesized compounds were evaluated for their osteogenic activity. Among the synthesized derivatives, four compounds showed significantly increased ALP activity. Among all four active compounds, the novel compound 3a has shown significant bone matrix mineralization and mRNA expressions of osteogenic marker genes, BMP2, RUNX-2 and OCN at 1 pM concentration.

Synthesis and biological evaluation of 21-arylidenepregnenolone derivatives as neuroprotective agents

A series of 21-arylidenepregnenolone derivatives and their corresponding epoxides were synthesized. The neuroprotective effects of these steroidal compounds against amyloid-β25-35 (Aβ25-35)- and hydrogen peroxide (H2O2)-induced neurotoxicity in PC12 cells, and oxygen-glucose deprivation (OGD)-induced neurotoxicity in SH-SY5Y cells were evaluated. The bioassay results indicated that several 3β-pregn-21-benzylidene-20-one derivatives displayed potent in vitro neuroprotective effects in different screening models, for example, compounds 2b, 3a, 3b, and 3s showing significant activities against Aβ 25-35-induced neurotoxicity in PC12 cells, 2b showing significant activities against H2O2-induced neurotoxicity in PC12 cells, and 2g, 3b, and 3e showing potent protection against OGD insult. The results suggested that introduction of an arylidene group into steroidal nucleus played an important role in neuroprotective activity, while the formation of epoxy group at C-5,6 could be also important for the neuroprotective activity in some degree. The pharmacological data reported here are helpful for the design of novel steroidal neuroprotective candidates.

Synthesis of pregnane derivatives, their cytotoxicity on LNCaP and PC-3 cells, and screening on 5α-reductase inhibitory activity

A series of epoxy-and/or 20-oxime pregnanes were synthesized from commercially available pregnenolone. Compounds 1, 3, 7, 8 and 11-13 were evaluated for cytotoxicity activity towards LNCaP (androgen-dependent) and PC-3 (androgenindependent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC50 15.17 μM) and PC-3 (IC50 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC50 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC50 68.95 μM), respectively. The 5α-reductase II (5AR2) inhibitory effects of compounds 1-3, 5 and 7-13 were investigated in a convenient screening model, in which compounds 5, 8, 11 and 12 were observed to be potential inhibitors of 5α-reductase, in particular, the 4-azasteroid 11, that also inhibited cell proliferation of androgen-dependent cells and 8, that in addition inhibited PC-3 cells more potently than LNCaP cells.

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.

Highly selective lipase-mediated discrimination of diastereomeric 5,6-epoxysteroids

Stereoisomerically pure 3β-hydroxy-5,6-epoxysteroids were obtained by combining selective chemical methods for α- and β-epoxidation of Δ5-unsaturated steroids with enzymatic stereoselective esterification of the 3β-hydroxyl group. 5β,6β-Epoxy-3β- hydroxysteroids were efficiently acylated by Novozym 435 and lipase AK, whereas 5α,6α-epoxy-3β-hydroxysteroids were good substrates for Candida rugosa lipase. Mild enzymatic deacylation of the 3β-acetoxy group in the presence of the epoxy functionality was also accomplished by C. rugosa lipase-mediated hydrolysis.