37413-91-5Relevant articles and documents
Optimization of the synthesis of a key intermediate for the preparation of glucocorticoids
Jouve, Romain,Thery, Vincent,Ducki, Sylvie,Helfenbein, Julie,Thiery, Jean-Christophe,Job, Aurélie,Picard, Elodie,Mallet, Christophe,Ripoche, Isabelle,Bennis, Khalil
, p. 14 - 21 (2018)
A short and efficient synthesis, based on a one-step double elimination, of a key intermediate in the synthesis of various glucocorticosteroids has been developed. This method can be carried out on large scale for further industrial applications. The synthesis allowed us to identify a novel prednisolone derivative 10 and its anti-inflammatory activity was determined in an in vivo model of inflammation. In order to understand the regioselectivity of the double elimination under various conditions, mechanistic studies were undertaken and confirmed the experimental results. We also propose a mechanism for the formation of the new steroid 10 studied by molecular modeling.
Preparation method of tetraene acetate
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Paragraph 0066-0086, (2019/12/25)
The invention discloses a preparation method of tetraene acetate. The preparation method of tetraene acetate comprises a step of subjecting a compound 2 as described in the specification, a free radical type halogenating reagent, sulfur dioxide and an acid-binding agent to a reaction in an organic solvent so as to obtain a compound 1 as described in the specification, i.e., tetraene acetate. According to the preparation method, easily and commercially available prednisolone low in price is used as a starting raw material, hydroxyl groups of two different configurations are simultaneously eliminated in the one-step reaction, and intracyclic alkene is formed; and the method is reduced in reaction steps, mild in reaction conditions, simple in aftertreatment, high in yield, high in the chemical purity of a crude product and suitable for industrial production.
Method for preparing tetraene acetate
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Paragraph 0021-0023; 0026; 0029; 0032; 0035; 0038, (2019/01/07)
The invention provides a method for preparing tetraene acetate. The method comprises the steps of subjecting a raw material, i.e., 17-ynepregna-1,4,9(11)-trien-3-one-17-hydroxyl acetate to a reactionin an organic solvent in the presence of a catalyst, i.e., palladium acetate and an oxidant, i.e., p-benzoquinone under the protection of inert gas so as to produce an intermediate, i.e., 18-hydroxylpregna-1,4,9(11),17-tetraen-3,19-dion-18-acetate, and carrying out treatment by using 1,8-diazabicycloundec-7-ene, thereby obtaining the tetraene acetate (21-hydroxylpregna-1,4,9(11),16-tetraen-3,20-dion-21-acetate)According to the method provided by the invention, the use of palladium chloride, copper chloride and oxygen is avoided, the corrosion to equipment is low, and meanwhile, the purity of the product is improved. The method has the advantages of being safe and efficient, being simple and convenient in operation, being satisfactory for industrial production, and the like and has a relatively high application value.