- Synthesis of novel 7α-thiol-bridged progesterone derivatives
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Novel synthetic routes to the formation of progesterone derivatives are of interest due to their potential role in the treatment of breast cancer. This multi-step synthesis proceeds via the dehydrogenation of the endocyclic ketone moiety of the steroid, a
- Wynne, James H.,Lloyd, Christopher T.,Mushrush, George W.
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- Manganese mediated oxidation of progesterone in alkaline medium: Mechanism study and quantitative determination
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We report here a non-immunosensing approach for the electrocatalytic oxidation of progesterone (P4) in alkaline medium using a salen-type manganese Schiff base complex (Mn(III)-SB) as a suitable electrocatalyst. We explored the role of carbon surface at glassy carbon electrode (GCE) and gold surface at glassy carbon/gold nanoparticles modified electrode (GCE/AuNPs) on immobilization of the Mn(III)-SB complex using cyclic voltammetry (CV) and density functional theory (DFT) calculations. The GCE/Mn(III)-SB displayed a pair of small redox peaks attributed to Mn(II)???Mn(III) with a small peak-to-peak separation (ΔEp), while GCE/AuNP/Mn(III)-SB displayed redox peaks with larger densities, but with a wider ΔEp. A combined molecular mechanics (MM) and quantum mechanics (QM) study were carried out to investigate the variation of surface configuration and energy barrier, when the Mn(III)-SB immobilization was modeled on GCE and GCE/Au surface. Cyclic voltammetry and hydrodynamic amperometry were used for the quantitative determination of P4. A limit of detection (LOD) of 11.4?nM was obtained using amperometry. The sensor retained 91% of its original response after 3 months, which is improved compared to previously reported P4 immunosensors. For the first time, a detailed mechanism for oxidation of P4 in alkaline medium was suggested. The proposed sensor was utilized to determine progesterone in milk samples.
- Shamsipur, Mojtaba,Pashabadi, Afshin,Taherpour, Avat (Arman),Bahrami, Kiumars,Sharghi, Hashem
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- Synthesis of 21-diazoprogesterone-6,7-3H2
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The preparation of 21-diazoprogesterone-6,7-3H2 is described. Progesterone was dehydrogenated with chloranil to give Δ6-dehydroprogesterone. Degradation of the pregnane side-chain with sodium hypobromite gave the corresponding carboxylic acid. Catalytic reduction with carrier-free tritium followed by treatment with oxalyl chloride and then diazomethane afforded 21-diazoprogesterone-6,7-3H2 with a specific activity of 42 Ci/mmol.
- Chiu,Wolff
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- Method and compound for synthetizing reprogestin
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To the synthesis method, dehydropregnenolone is taken as a starting material, carbonyl-protected dehydropregnenolone is prepared, and then a methyl configuration overturning compound is obtained through photo-catalytic reaction and further subjected to deprotection. Hydroxylation and double bond rearrangement reaction yield progestin. The method has the advantages of easily available raw materials, high yield and simple and mild reaction conditions, and is suitable for industrial production of progestin.
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- Method for synthesizing dydrogesterone
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The invention relates to a method for synthesizing a steroid drug dydrogesterone (CAS: 152-62-5). The method comprises the following steps: starting from pregnenolone, carrying out allylic halogenation and elimination to obtain a Pregna-5, 7-dien-3-ol-20-one intermediate; carrying out illumination isomerization to obtain a key intermediate 9 beta, 10 alpha-Pregna-5, 7-dien-3-ol-20-one; then carrying out Oppenauer oxidation (Oppenauer oxidation) to obtain 7-Dehydro-9beta, 10 alpha-progesterone, and finally, carrying out olefin shift isomerization under the action of acid to obtain the final product 6-Dehydro-9beta, 10 alpha-progesterone (a crude drug of dydrogesterone). The method is economical in steps and comprises four conversion steps; the total yield is as high as 16.4%; the raw materials are cheap and easy to obtain, the whole process route is green and safe, the bulk drugs are high in quality, the purity can reach 99.5% or above, and the method is suitable for industrial production.
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Paragraph 0029-0031
(2021/05/19)
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- Production process capable of industrially synthesizing dydrogesterone
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The invention discloses a production process capable of industrially synthesizing dydrogesterone. Easily available progesterone is used as a raw material, and dydrogesterone is prepared through the steps of carbonyl protection, bromination, debromination, photochemical ring-opening reaction, photochemical ring-closing reaction, deprotection and double bond isomerization. The production process hasthe advantages of easily available initial raw materials, and easiness in implementation of each step and higher yield; the production process is simple and convenient to operate, is green and environment-friendly, and can be easily amplified to industrial production.
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- Preparation method for 5,7-pregnadien-3,20-dion-diethylene glycol ketal
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The invention provides a preparation method for 5,7-pregnadien-3,20-dion-diethylene glycol ketal. The method comprises the following steps: performing an etherification reaction on progesterone and anetherification agent under the action of a catalyst to generate an ether; performing a dehydrogenation reaction on the ether and a dehydrogenation reagent to generate 6-dehydroprogesterone; and performing ketalation on the 6-dehydroprogesterone and ethylene glycol under the action of a catalyst and a dehydrating agent to generate the 5,7-pregnadien-3,20-dion-diethylene glycol ketal. The 5,7-pregnadien-3,20-dion-diethylene glycol ketal with less impurities can be obtained through the etherification, dehydrogenation reaction and ketalation, and the method has the advantages of a short route, ahigh yield, low raw material costs, simple operation and environmental protection, and is suitable for industrial production.
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- PROCESS FOR PREPARATION OF DYDROGESTERONE
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The present invention relates to process for the preparation of dydrogesterone.
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- A pregnane -16 - ene - 3, 20 - dione steroid derivatives preparation method (by machine translation)
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The invention relates to a pregnane - 16 - ene - 3, 20 - dione steroid derivatives (II) of the preparation method, is characterized in that the 17 preparation ethynyl - 17 hydroxy steroid derivatives I prepares the side with the reagent A or containing reagent A organic solvent reaction, reaction temperature: 25 °C - solvent reflux temperature, said reagent A is 7 - 15 weight percent of the phosphorus pentoxide dissolved in methanesulfonic acid solution that is formed 17 preparation ethynyl - 17 prepares the side hydroxy steroid derivatives (I) obtained in the reaction with the reagent A, reaction temperature: 25 °C - solvent reflux temperature, said reagent A is 7 - 15% weight percent of phosphorus pentoxide is dissolved in methanesulfonic acid solution that is formed. (by machine translation)
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Paragraph 0030; 0031; 0032
(2018/06/14)
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- Effective and mild method for converting 3β-hydroxysteroids to 3-keto steroids via DDQ/TEMPO
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A mild and efficient oxidation of 3β-hydroxysteroids to the corresponding 3-keto steroids can be carried out at room temperature, using DDQ in the presence of catalytic TEMPO. Oxidation of saturated 3β-hydroxysteroids gave the corresponding ketones in excellent yield. The 5-unsaturated 3β-hydroxysteroids are oxidized selectively to 4-en-3-one or 4,6-diene-3-one derivatives according to the amount of DDQ in reaction. This is a good method for the synthesis of 4,6-diene-3-one from the corresponding 3β-hydroxy-5-ene steroids. Meanwhile, configurations of the oxidation compounds 2a, 2b, 3b, 2c, 2f and 2g were identified by X-ray diffraction. A possible mechanism is presented and discussed.
- Zhang, Wu,Pan, Dan,Wu, Aiqun,Shen, Liqun
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- Progesterone-adenine hybrids as bivalent inhibitors of P-glycoprotein- mediated multidrug efflux: Design, synthesis, characterization and biological evaluation
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Bivalent ligands were designed on the basis of the described close proximity of the ATP-site and the putative steroid-binding site of P-glycoprotein (ABCB1). The syntheses of 19 progesterone-adenine hybrids are described. Their abilities to inhibit P-glycoprotein-mediated daunorubicin efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein were evaluated versus progesterone. The hybrid with a hexamethylene linker chain showed the best inhibitory potency. The efficiency of these progesterone-adenine hybrids depends on two main factors: (i) the nature of the linker and (ii) its attachment point on the steroid skeleton.
- Zeinyeh, Wael,Mahiout, Zahia,Radix, Sylvie,Lomberget, Thierry,Dumoulin, Axel,Barret, Roland,Grenot, Catherine,Rocheblave, Luc,Walchshofer, Nadia,Matera, Eva-Laure,Dumontet, Charles
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p. 1177 - 1191,15
(2020/08/20)
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- NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE
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The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.
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Page/Page column 22
(2011/07/07)
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- C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump
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The P-glycoprotein product (Pgp) of the MDR1 gene has been implicated in the multiple drug resistance phenotype expressed by many cancers. Functioning as an efflux pump, P-glycoprotein prevents the accumulation of high intracellular concentrations of subs
- Leonessa, Fabio,Kim, Ji-Hyun,Ghiorghis, Alem,Kulawiec, Robert J.,Hammer, Charles,Talebian, Abdelhossein,Clarke, Robert
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p. 390 - 398
(2007/10/03)
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- SYNTHESIS OF Δ6-, Δ1,6-, AND Δ1,6,16-PROGESTERONE
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The reaction of bromine and progesterone in a molar ratio of 2:1 leads to the formation mainly of 2,6-dibromoprogesterone, while reaction in a ratio of 3:1 gives 2,6,16-tribromoprogesterone.Their dehydrobromination in boiling lutidine leads to Δ1,6- and Δ1,6,16-progesterone.The dehydrogenation of progesterone by chloranil in tert-butyl alcohol gives Δ6-progesterone with a yield of 48percent.
- Kogan, N. A.,Raskin, L. M.,Vlasova, M.I.,Kul'bitskaya, S. M.
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p. 883 - 884
(2007/10/02)
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- Synthesis of the 6-Methylencarboxylic Acid Derivatives of Testosterone and Progesterone
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The methyl 6β-(phenylsulfonyl)acetate and methyl 6β-(methylsulfonyl)acetate derivatives 8 and 10, respectively, of testosterone and of progesterone (9 and 11, respectively) were synthesized by allylic alkylation of the corresponding ?-allylpalladium chloride complexes 3 and 4.Chromatographic separation of the reaction mixtures yields as main products 8a and 9a with S configuration at the new asymmetric center.By-products 8b and 9b have R configuration.The corresponding by-products were not found in reaction mixtures of 10 and 11.The by-products 9c and 11c with α-configuration at C-17 (isoprogesterone derivatives) were isolated from the corresponding reaction mixtures.Alkaline treatment of the main products leads to the 6-methylenecarboxylic acid derivatives as a result of elimination and saponification: 8a and 11a gave 16 and 17.Base-catalyzed elimination of 9a yields the α,β-unsaturated methyl ester 19.NMR spectroscopic investigations (NOE, NOESY) of 19 support the predicted E configuration.
- Handschuh, Dieter,Voelter, Wolfgang
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p. 1007 - 1016
(2007/10/02)
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- Conversion of Enones into Dienones via Allylpalladium Complexes
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A series of reagents for the conversion of enones into dienones via allylpalladium compounds has been studied and mild conditions for dienone preparation are recommended.
- Haynes, Richard K.,Jackson, Roy W.,Stragalinou, Anna
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p. 1537 - 1544
(2007/10/02)
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- 3-Keto-7 α,β-loweralkyl-Δ 5-steroids
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7(α,β)-Loweralkyl-3-keto-Δ 5 -androstanes and 7(α,β)-loweralkyl-3-keto-Δ 5 -pregnanes having anabolic, androgenic, claudogenic, progestational and anti-progestational properties are prepared by reacting 3-keto-4,6-dienic androstanes and pregnanes with organocopper reagents such as dialkyllithium cuprate. The isomerization of these compounds to yield 7(α,β)-loweralkyl-3-keto-Δ 4 -steroids is also described.
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