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.
A novel synthesis of steroidal Δ4,3,6-diones using pyridinium chlorochromate (PCC)
Parish,Kizito,Heidepriem
, p. 223 - 230 (1993)
Pyridinium chlorochromate (PCC), in refluxing benzene, has been found to be an effective and convenient reagent for the oxidation of steroidal Δ5-3β-tetrahydropyranyl ethers to the corresponding Δ4-3,6-diones in high yield.
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).
Oxidation of homoallylic steroidal alcohols with pyridinium chlorochromate. The synthesis of steroidal 4-en-3,6-diones
Blaszczyk,Paryzek
, p. 3255 - 3259 (1994)
Prolonged oxidation of steroidal homoallylic Δ5-3-alcohols with pyridinium chlorochromate (PCC) in dichloromethane affords the corresponding Δ4-3,6-diones via the intermediate Δ5-3-one and not a Δ4-3-one.
A novel oxidation of homoallylic alcohols under sonochemical conditions
Miranda Moreno,Sa E Melo,Campos Neves
, p. 3201 - 3204 (1991)
The oxidation of 3β-hydroxy-Δ5-cholestenes, -pregnenes and -androstenes to the corresponding Δ4-3,6-diones has been achieved in high yields by a new one-step process, using tetra-n-propylammonium perruthenate with 4-methylmorpholine N-oxide as co-oxidant, under sonochemical conditions.
OXIDATION WITH SODIUM PEROXIDE. DIRECT INTRODUCTION OF A γ CARBONYL GROUP INTO α,β UNSATURATED KETOSTEROIDS
Holland, Herbert L.,Daum, Ulrich,Riemland, Elly
, p. 5127 - 5128 (1981)
Aqueous sodium peroxide oxidises the conjugated Δ4-3-ketosteroids 1a-1d to the corresponding Δ4-3,6-diones in good yield.Saturated carbonyl and alcohol groups are not affected by the reaction.
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.
Facile synthesis of steroidal Δ4-3,6-diones from Δ5-3-ols using pyridinium chlorochromate
Nangia,Anthony
, p. 225 - 230 (1996)
Pyridinium chlorochromate (PCC) in dichloromethane under ambient conditions is found to oxidise steroidal Δ5-3-alcohols to Δ4-3,6-diketones in high yield.
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.
Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity
Campos Neves, Andre S.,Sa E Melo, Maria Luisa,Moreno, Maria Jose S. M.,Tavares Da Silva, Elisiario J.,Salvador, Jorge A. R.,Da Costa, Saul P.,Martins, Rosa Maria L. M.
, p. 3255 - 3264 (1999)
An Henbest reduction, followed by the preparation of a silyl enol ether and oxidation in situ with m-CPBA has led to the neurosteroids 3α-hydroxy- and 3α,21-dihydroxy-5α-pregnanolones. Using testosterone as starting material, a new short synthesis of an aromatase inhibitor, 4-OHA, has been achieved through hydroboration/oxidation followed by a Swern type oxidation and epimerization. Another aromatase inhibitor, androst-4-ene-3,6,17-trione, has been efficiently prepared using PCC on montmorillonite K10, under ultrasonic irradiation.
