8056-11-9

Upstream product

• 50-23-7 HYDROCORTISONE 
• 566-35-8 Epicortisol 
• 53-03-2 Prednison 
• 1249-67-8 17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate 
• 2920-86-7 prednisolone hemisuccinate 
• 3331-71-3 21-<<(6-carboxy-3-cyclohexen-1-yl)carbonyl>oxy>-11β,17α-dihydroxypregna-1,4-diene-3,20-dione 
• 1107-99-9 prednisolone 21-trimethylacetate 
• 52-21-1 prednisolone 21-acetate 
• 30934-01-1 17α-Hydroxy-pregna-1,4,9(11)-dien-3,20-dion 
• 640-87-9 cortexolone 21-acetate 
• 1807-14-3 17α,21-dihydroxypregna-1,4-diene-3,20-dione 
• 10184-69-7 (10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one 
• 4380-55-6 pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate 
• 73771-04-7 prednicarbate 

Downstream Products

• 86678-37-7 21-phenoxyacetoxy-11,17-dihydroxy-pregn-1,4-diene-3,20-dione 
• 57073-10-6 methyl (20S)-11β,17,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate 
• 2205-88-1 Prednisolone 21-ethylcarbonate 
• 53770-95-9 (1S,2S,3aS,4R,6aS)-4-Hydroxy-4-(2-hydroxy-acetyl)-1-[2-(5-hydroxy-2-methyl-phenyl)-ethyl]-3a-methyl-octahydro-pentalene-2-carbaldehyde 
• 104286-02-4 Prednisolone 17-ethylcarbonate 
• 1426535-35-4 C₂₉H₃₃NO₈ 
• 1426535-37-6 C₃₀H₃₅NO₈ 
• 133991-62-5 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride 
• 898-84-0 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione 
• 95825-22-2 C₃₀H₃₆O₆ 
• 1415405-04-7 C₄₁H₄₈N₂O₈ 
• 53789-72-3 (3aS,4S,5S,6aS)-5-Hydroxymethyl-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-6a-methyl-hexahydro-pentalen-1-one 
• 53771-01-0 (1S,3aS,4S,5S,6aS)-5-Hydroxymethyl-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-1,6a-dimethyl-octahydro-pentalen-1-ol 

Relevant academic research and scientific papers

Preparation method of prednisolone acetate

The invention relates to prednisolone acetate and a preparation method of prednisolone acetate, which are characterized in that the prednisolone acetate is prepared by sequentially carrying out a biological fermentation, an esterification reaction, a bromination reaction and a debromination reaction on the raw material, the prednisolone acetate is subjected to a hydrolysis reaction to obtain prednisolone, the overall yield is up to 81.75%, and the HPLC area normalization content of prednisolone is up to 99.5%. The preparation method is short in synthetic route and low in cost, is suitable forindustrial production, and has a very high industrial value.

Dehalogenation methodof 9-halogenated steroid compound and application

The invention provides a dehalogenation method of a 9-halogenated steroid compound and application, and relates to the technical field of chemical synthesis. The dehalogenation method of the 9-halogenated steroid compound comprises the following steps: reacting a compound I with a hydrogen donor and an azo radical initiator to obtain a 9-dehalogenated product compound II of the 9-halogenated steroid compound. According to the dehalogenation method of the 9-halogenated steroid compound, a hydrogen donor adopts one or a combination of more of hypophosphorous acid and hypophosphite, formic acid and formate, organic silicon hydride, hydrazine compounds or cyclohexene, and an initiator adopts an azo free radical initiator. Reagents such as chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride which are high in toxicity and cause serious pollution to the environment are not used in the reaction, the method is green and environmentally friendly, the synthesis process is simple, convenient and easy to implement, and the production applicability is improved.

Δ1-dehydrogenation and C20 reduction of cortisone and hydrocortisone catalyzed by rhodococcus strains

Prednisone and prednisolone are steroids widely used as anti-inflammatory drugs. Development of the pharmaceutical industry is currently aimed at introducing biotechnological processes and replacing multiple-stage chemical syntheses. In this work we evaluated the ability of bacteria belonging to the Rhodococcus genus to biotransform substrates, such as cortisone and hydrocortisone, to obtain prednisone and prednisolone, respectively. These products are of great interest from a pharmaceutical point of view as they have higher anti-inflammatory activity than the starting substrates. After an initial lab-scale screening of 13 Rhodococcus strains, to select the highest producers of prednisone and prednisolone, we reported the 200 ml-batch scale-up to test the process efficiency and productivity of the most promising Rhodococcus strains. R. ruber, R. globerulus and R. coprophilus gave the Δ1-dehydrogenation products of cortisone and hydrocortisone (prednisone and prednisolone) in variable amounts. In these biotransformations, the formation of products with the reduced carbonyl group in position C20 of the lateral chain of the steroid nucleus was also observed (i.e., 20β-hydroxy-prednisone and 20β-hydroxy-prednisolone). The yields, the absence of collateral products, and in some cases the absence of starting products allow us to say that cortisone and hydrocortisone are partly degraded.

Facile synthesis of corticosteroids prodrugs from isolated hydrocortisone acetate and their quantum chemical calculations

In the present research paper corticosteroids prodrugs of hydrocortisone acetate (1) have been synthesized, which was isolated from the flowers of Allamanda Violacea. The hydrocortisone acetate (1) was hydrolyzed to hydrocortisone (2) which was subsequently converted to prednisolone (3). Both the hydrocortisone (1) and prednisolone (2) underwent Steglich esterification with naproxen and Ibuprofen yielding compounds 11, 17 dihydroxy-21-(2-(6-methoxynaphthalene-2yl) propionoxy)-pregn-4-ene-3, 20-dione (4), 11, 17-dihydroxy-21-(2-(4-isobutylphenyl) propionoxy)-pregn-4-ene-3, 20-dione (5), 21-(2-(6-methoxynaphthalene-2-yl) propionoxy) 11,17-di-hydroxy-3,20-diketo-pregn-1,4-diene (6) and 11,17-di-hydroxy-3,20-diketo-pregn-1,4-diene-21-yl-2-(4-isobutylphenyl) propanoate (7). The synthesized compounds have been characterized with the help of spectroscopic techniques like 1H, 13C NMR, FT-IR spectroscopy and mass spectrometry. Density functional theory (DFT) with B3LYP functional and 6-31G (d, p) basis set has been used for the Quantum chemical calculations. The electronic properties such as frontier orbitals and band gap energies were calculated by TD-DFT approach. Intramolecular interactions have been identified by AIM (Atoms in Molecule) approach and vibrational wavenumbers have been calculated using DFT method. The reactivity and reactive site within the synthesized prodrugs have been examined with the help of reactivity descriptors. Dipole moment, polarizability and first static hyperpolarizability have been calculated to get a better insight of the properties of synthesized prodrugs. The molecular electrostatic potential (MEP) surface analysis has also been carried out.

Characterization of new recombinant 3-ketosteroid-Δ1-dehydrogenases for the biotransformation of steroids

3-Ketosteroid-Δ1-dehydrogenases (KstDs [EC 1.3.99.4]) catalyze the Δ1-dehydrogenation of steroids and are a class of important enzymes for steroid biotransformations. In this study, we cloned 12 putative KstD-encoding (kstd) genes from both fungal and Gram-positive microorganisms and attempted to overproduce the recombinant proteins in E. coli BL21(DE3). Five successful recombinant enzymes catalyzed the Δ1-desaturation of a variety of steroidal compounds such as 4-androstene-3,17-dione (AD), 9α-hydroxy-4-androstene-3,17-dione (9-OH-AD), hydrocortisone, cortisone, and cortexolone. However, the substrate specificity and catalytic efficiency of the enzymes differ depending on their sources. The purified KstD from Mycobacterium smegmatis mc2155 (MsKstD1) displayed high catalytic efficiency toward hydrocortisone, progesterone, and 9-OH-AD, where it had the highest affinity (Km 36.9?±?4.6?μM) toward 9-OH-AD. On the other hand, the KstD from Rhodococcus erythropolis WY 1406 (ReKstD) exhibited high catalytic efficiency toward androst-4,9(11)-diene-3,17-dione (Diene), 21-acetoxy-pregna-4,9(11),16-triene-3,20-dione (Triene), and cortexolone, where in all three cases the Km values (12.3 to 17.8?μM) were 2.5–4-fold lower than that toward hydrocortisone (46.3?μM). For both enzymes, AD was a good substrate although ReKstD had a 3-fold higher affinity than MsKstD1. Reaction conditions were optimized for the biotransformation of AD or hydrocortisone in terms of pH, temperature, and effects of hydrogen peroxide, solvent, and electron acceptor. For the biotransformation of hydrocortisone with 20?g/L wet resting E. coli cells harboring MsKstD1 enzyme, the yield of prednisolone was about 90% within 3?h at the substrate concentration of 6?g/L, demonstrating the application potential of the newly cloned KstDs.

A process for the preparation of prednisolone

The application relates to a method for synthetizing prednisolone. Double bond bromination, reductive debromination, bromination and hydrolysis reaction are carried out on a compound with a structure of formula I so as to generate the prednisolone. The method is high in yield, is easy to operate, and is applicable to industrial production.

A process for the preparation of prednisolone (by machine translation)

The invention relates to a process for the preparation of prednisolone, including: to ACOH predinisone as raw materials, sequentially through the 3,20-keto-protection reaction and 11-keto-reduction reaction, 21-position hydroxy esterification reaction, 3,20- position alkone remove protection reaction, 21-bit b ester hydrolysis reaction is prednisolone. The present invention provides a first esterification, then deprotected of the new synthetic route, the deprotected process the nitrosation quenching reaction and resin hydrolysis reaction; an ester reaction in the mixed solvent and to complete the protection of inert gas, to avoid the hydrolysis reaction produces by-products. Process route of this invention is novel, the operation process is simple, the production cost is low, is suitable for industrial scale production. (by machine translation)

Microbial transformation of topical corticosteroid: Prednicarbate

In the present research, the steroidal antiinflammatory topically used drug prednicarbate (1) was subjected to microbial biotransformation by Cunninghamella elegans. Prednicarbate (1) was transformed into various metabolites. One new and two known metabolites were purified named as prednisolone 17-ethylcarbonate (2) Prednisolone (3) and 4-(4-hydroxybenzyl)-2-(3-methylbut-2-enyl)phenyl methyl carbonate (4). The compound (4) was separated as a new compound and was not reported in literature. Its structure did not show resemblance with prednicarbate so possibly derived from fungal mass. Their structures were elucidated by using modern spectroscopic techniques e.g. 13C NMR, 1H NMR, HMQC, HMQC, COSY, NOESY and mass spectrometry e.g. EI-MS.

A nitrophenyl-based prodrug type for colorectal targeting of prednisolone, budesonide and celecoxib

Celecoxib is a COX-2 inhibitor drug that can be used to reduce the risk of colorectal adenocarcinoma. Glucocorticoids are used in the treatment of inflammatory bowel disease. A limitation to the use of both drug types is that they undergo absorption from the intestinal tract with serious side effects. The prodrug systems introduced here involve forming a nitro-substituted acylsulfonamide group in the case of celecoxib and a nitro-substituted 21-ester for the glucocorticoids. Drug release is triggered by the nitro reductase action of the colonic microflora, liberating a cyclization competent species. The release of the active parent drugs was evaluated in vitro using Clostridium perfringens and epithelial transport through Caco-2 monolayer evaluation was carried out to estimate the absorption properties of the prodrugs compared to the parental drugs.

FLUOROQUINOLONE DERIVATIVES FOR OPHTHALMIC APPLICATIONS

The present invention relates to fluoroquinolone derivatives having enhanced ocular penetration characteristics and/or antimicrobial activity, and to compositions comprising such derivatives. The derivatives and compositions are particularly well suited for treating ophthalmic bacterial infections. The present invention more particularly relates to the discovery that a 2-methyl substitution on a diazabicyclo group attached to a fluoroquinolone ring system produces improved permeability characteristics, and that a 5-amino substitution on a fluoroquinolone ring system results in improved anti-microbial activity.