19289-53-3Relevant academic research and scientific papers
B-cholesterol-reducingoxidation derivativeand synthesis method and application thereof
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, (2019/06/30)
The invention provides a B-cholesterol-reducingoxidation derivative. The structural formula of the compound is as shown in the description, wherein, R is CH3 or CH3CH2CH2 or CH3CH2CH2CH2. The B-cholesterol-reducingoxidation derivativecompound can significantly inhibit growth and proliferation of tumor cellsof human breast cancer cells, human ductalbreast cancer cells and human ovarian cancer cells,and can be used as drug intermediates or drugs and applied to manufacturing and use of different drugs.
Ozonolysis of cholesterol and other Δ5-steroids in the presence of alcohols: A revised mechanism and hydroperoxide structure of the solvent-participated product, confirmed by X-ray analysis
Paryzek, Zdzislaw,Rychlewska, Urszula
, p. 2313 - 2318 (2007/10/03)
The structure of the product formed in the course of the reaction of cholesterol acetate and other Δ5-steroids with ozone in alcohol-containing solvents has been revised. The solvent-participated products are hydroperoxides, 5α-hydroperoxy-7α-alkoxy-5α-B-homo-6-oxasteroids 3 and not the previously claimed cyclic hemiperacetals, 5α-hydroxy-7α-alkoxy-B-dihomo-6,7-dioxacholestane derivatives 1. The final evidence has been obtained from X-ray crystal structure analysis of the selected hydroperoxides 3a, 3c and 3j. It is proposed that hydrogen bonding involving the hydroperoxy and the alkoxy group is responsible for the stability of these hydroperoxides and also exerts a directive effect in the nucleophilic attack on the Criegee intermediate 12 by the alcohol.
The Reaction of Cholesterol with Ozone and Alcohols: a Revised Mechanism and Structure of the Principal Product
Paryzek, Zdzislaw,Martynow, Jacek,Swoboda, Witold
, p. 1222 - 1223 (2007/10/02)
The structure of the product formed in the course of the reaction of cholesterol acetate with ozone in alcohol-containing solvents has been revised.In methanol-chloroform, it is shown to be the hydroperoxide, 3β-acetoxy-5α-hydroperoxy-7β-methoxy-5α-B-homo-6-oxacholestane (8a), and not the previously claimed, cyclic hemiperacetal, 3β-acetoxy-5-hydroxy-7a-methoxy-B-dihomo-6,7-dioxacholestane (1; R1=Ac, R2=Me).
Ozonization of Cholesterol in Nonparticipating Solvents
Jaworski, Krzysztof,Smith, Leland L.
, p. 545 - 554 (2007/10/02)
Reaction of ozone with cholesterol (or cholesterol 3β-acetate) in dilute CCl4 or hexane solutions gave the heretofore undescribed isomeric 1,2,4-trioxolane ozonides 5,7α-epidioxy-5α-B-homo-6-oxacholestan-3β-ol and 5,7β-epidioxy-5β-B-homo-6-oxacholestan-3β-ol (or their 3β-acetates).Structures are supported by proton and carbon spectra and by Zn/acetic acid reduction to 3β-hydroxy(or 3β-acetoxy)-5-oxo-5,6-secocholestan-6-al.At higher cholesterol concentrations oxidized dimeric and oligomeric products are formed at the expense of 1,2,4-trioxolane ozonides.The major dimer 6ξ-(cholest-5'-en-3'β-yloxy)-5,6ξ-epidioxy-5ξ-5,6-secocholestane-3β,5-diol formed monoesters and was reduced by Zn/acetic acid to equivalent amounts of 3β-hydroxy-5-oxo-5,6-secocholestan-6-al and cholesterol.Also formed from cholesterol were dimeric ozonides 6ξ-(5',7'α-epidioxy-5'α-B'-homo-6'-oxacholestan-3'β-yloxy)-5,6ξ-epidioxy-5ξ-5,6-secocholestane-3β,5-diol and 6ξ-(5',7'β-epidioxy-5'β-B'-homo-6'-oxacholestan-3'β-yloxy)-5,6ξ-epidioxy-5ξ-5,6-secocholestane-3β,5-diol and dimeric epoxides 5,6ξ-epidioxy-6ξ-(5',6'α-epoxy-5'α-cholestan-3'β-yloxy)-5ξ-5,6-secocholestane-3β,5-diol and 5,6ξ-epidioxy-6ξ-(5',6'β-epoxy-5'β-cholestan-3'β-yloxy)-5ξ-5,6-secocholestane-3β,5-diol.Oligomeric 1,2,4-trioxolane ozonide isomers were also formed.Ozone thus reacts with cholesterol in two ways, by epoxidation and putatively by carbonyl oxide formation, with subsequent carbonyl oxide cyclization to 1,2,4-trioxolane ozonides or interception of cholesterol, cholesterol epoxides, and cholesterol ozonides (as alcohols) to yield dimeric and oligomeric species.
