2243-06-3Relevant articles and documents
An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3β-ols using a modified Jones oxidation methodology
Hunter, A. Christy,Priest, Shelley-Marie
, p. 30 - 33 (2006)
Steroids with 4-ene-3,6-dione functionality have application in natural product chemistry, as synthetic intermediates and as aromatase inhibitors. Here, we report a two-phase oxidation of a range of steroidal 5-en-3β-ols into corresponding 4-ene-3,6-diones using a modified Jones oxidation. The new reaction affords high yields (77-89%) of product in relatively short reaction times (1-2 h). The simplicity of this reaction gives significant advantages over previously reported methodologies.
Oxidation of steroidal 5-en-3β-ols with Jones reagent in ether
Solaja, Bogdan A.,Mili, Dragana R.,Do, Ljiljana I.
, p. 330 - 334 (1994)
The two-phase oxidation of steroidal 5-en-3β-ol (via 5-en-3-ones) into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent was investigated. It was found that the system Jones reagent/diethyl ether enables short reaction times and easy isolation of the obtained products. The exclusive abstraction of 4α-hydrogen during oxidation, together with molecular mechanics (MM2), and semiempirical (PM3) calculations, suggest that boat conformation of ring A precedes the formation of corresponding radicals (or cations).
Barry et al.
, p. 379 (1963)
Koerner
, p. 880 (1969)
Pyridinium dichromate: A novel reagent for the oxidation of steroidal Δ5-3β-alcohols to the corresponding Δ4-3,6-diketones
Hector, Markus,Hartmann, Rolf W.,Njar, Vincent C. O.
, p. 1075 - 1082 (1996)
A novel procedure for the direct conversion of steroidal Δ5-3β-alcohols to the corresponding Δ4-3,6-diketones in high yield (66-85%) has been achieved using pyridinium dichromate (PDC) in dimethylformamide (DMF) at room temperature.
Orr,Broughton
, p. 1949,1950 (1975)
Synthesis and biological evaluation of steroidal derivatives as selective inhibitors of AKR1B10
Zhang, Wei,Wang, Ling,Zhang, Liping,Chen, Wenli,Chen, Xinying,Xie, Minyu,Yan, Guangmei,Hu, Xiaopeng,Xu, Jun,Zhang, Jingxia
, p. 39 - 44 (2014)
AKR1B10 is a member of human aldo-keto reductase superfamily, and a promising anti-cancer therapeutic target. In this paper, androst-5-ene-3β- ol, dehydroepiandrosterone, pregnenolone and cholesterol were used as reactants, sixteen products were obtained through Jones reaction and reduction reaction using NaBH4. Their inhibitory activities against AKR1B10 and AKR1B1 were measured. The most active compound (3a) has the IC50 of 0.50 μM for AKR1B10, and the most AKR1B10 selective compound (2a) has the IC 50 of 0.81 μM with AKR1B1/AKR1B10 selectivity of 195. In addition, the binding modes of 2a and 3a in the active site of human AKR1B10 were identified by docking.
Novel approach to the synthesis of istaroxime
Liang,Guo,Jiang
, p. 2643 - 2647 (2017/12/26)
Istaroxime 1, a novel cardiotonic agent with high efficiency and low toxicity was synthesized from dehydroepiandrosterone 2 using a novel approach that included epoxidation, ring-opening, substitution, and oximation. The new protocol without gas protection was milder than the reported approaches. The overall yield of the method was 24.1%.
Development of a Chemoenzymatic Process for Dehydroepiandrosterone Acetate Synthesis
Fryszkowska, Anna,Peterson, Justine,Davies, Nichola L.,Dewar, Colin,Evans, George,Bycroft, Matthew,Triggs, Neil,Fleming, Toni,Gorantla, Srikanth Sarat Chandra,Hoge, Garrett,Quirmbach, Michael,Timmanna, Upadhya,Reddy Poreddy, Srinivas,Kumar Reddy, D. Naresh,Dahanukar, Vilas,Holt-Tiffin, Karen E.
, p. 1520 - 1528 (2016/08/30)
Dehydroepiandrosterone (DHEA, 2) is an important endogenous steroid hormone in mammals used in the treatment of a variety of dysfunctions in female and male health,1 as well as an intermediate in the synthesis of steroidal drugs, such as abiraterone acetate which is used for the treatment of prostate cancer.2-4 In this manuscript we describe a novel, concise, and cost-efficient route toward DHEA (2) and DHEA acetate (3) from 4-androstene-3,17-dione (4-AD, 1). Crucial to success was the identification of a ketoreductase from Sphingomonas wittichii for the highly regio- and stereoselective reduction of the C3-carbonyl group of 5-androstene-3,17-dione (5) to the required 3β-alcohol (2, >99% de). The enzyme displayed excellent robustness and solvent stability under high substrate concentrations (up to 150 g/L).
