合成路线:1) By the reaction of 4-methyl-3-oxo-4-aza-5alpha-androstane-17beta-carboxylic acid (I) with diisopropylcarbodiimide (II) in methylene chloride at room temperature.
合成路线:2) By the reaction of 3-oxoandrost-4-ene-17beta-carboxylic acid (III) with diisopropylcarbodiimide (II) in refluxing ethyl acetate and subsequent A-ring opening of compound (IV) by treatment with the Lamieux-von Rudloff reagent (permanganate-periodate) in isopropanol.The cyclization of the secoacid (V) so obtained,with methylamine in dioxane under pressure,followed by the hydrogenation under pressure,on 10% Pd/C in ethanol,affords turosteride.This method is used for the large scale production of turosteride.
参考文献标题:Turosteride
文献作者:Di Sale,E.; Panzeri,A.
参考来源:Drugs Fut 1993,18(5),436
合成路线:The synthesis of [14C]-turosteride has been reported:The reaction of 20-[14C]-3-hydroxy-5-pregnen-20-one (I) with iodine and pyridine gives the pyridinium derivative (II),which is treated with sodium methoxide and methanol yielding 3-hydroxy-5-androstene-17beta-carboxylic acid methyl ester (III).The oxidation of (III) with cyclohexanone and aluminum isopropoxide affords 3-oxo-5-androstene-17beta-carboxylic acid methyl ester (IV),which is oxidized with potassium permanganate and sodium periodate to the propionic acid derivative (V).The cyclization of (V) with methylamine in diglyme at 180 C affords 4-methyl-3-oxo-4-aza-5-androstene-17beta-carboxylic acid methyl ester (VI),which is hydrogenated with H2 over PtO2 in acetic acid to the corresponding saturated compound (VII).The saponification of (VII) with KOH in refluxing methanol/water gives the 4-methyl-3-oxo-4-aza-5alpha-androstane-17beta-carboxylic acid (VIII),which is finally condensed with diisopropylcarbodiimide (IX) in refluxing dichloromethane.
参考文献标题:Synthesis of carbon-14 labelled 1-[4-methyl-3-oxo-4-aza-5alpha-androstane-17beta-carbonyl]-1,3-diisopropylurea (turosteride),a new 5alpha-reductase inhibitor
文献作者:Panzeri,A.; Dostert,P.; Angiuli,P.; Fontana,E.; Pignatti,A.
参考来源:J Label Compd Radiopharm 1996,38(7),667
合成路线:1) By the reaction of 4-methyl-3-oxo-4-aza-5alpha-androstane-17beta-carboxylic acid (I) with diisopropylcarbodiimide (II) in methylene chloride at room temperature.
参考文献标题:Azasteroids as inhibitors of rat prostatic 5alpha-reductase
文献作者:Rasmusson,H.G.; Reynolds,G.F.; Utne,T.; Jobson,R.B.; Primka,R.L.; Berman,C.; Brooks,J.R.
参考来源:J Med Chem 1984,27(12),1690-701
产品链接: CAS No. 137099-09-3››