【药物名称】EpiBr, HE-2000, Immunitin, Inactivin
化学结构式(Chemical Structure):
参考文献No.597164
标题:Inhibition of HIV replication: Synthesis of [4-14C]-5alpha-androstan-16alpha-bromo-3 beta-ol-17-one
作者:Han, M.C.; Hayes, B.A.; Prendergast, P.T.; Gupta, S.
来源:J Label Compd Radiopharm 2000,43(12),1149
合成路线图解说明:

Alternatively, the title compound was directly obtained by bromination of epiandrosterone (I) with cupric bromide in refluxing MeOH

合成路线图解说明:

The reaction of testosterone (I) with isobutylene (II) in dichloromethane catalyzed by trifluoromethanesulfonic acid gives the tert-butyl ether (III), which is ozonolyzed with O3 and H2O2 in AcOH/ethyl acetate to yield the seco-steroid (IV). The cyclization of (IV) by means of acetic anhydride and potassium acetate at 135 C affords the 4-oxa steroid (V), which is methylated with 14C-labeled methylmagnesium iodide in ether to provide the intermediate (VI). The rearrangement of (VI) by means of NaOH in ethanol gives the labeled testosterone tert-butyl ether (VII), which is deprotected by means of 6N HCl in refluxing ethanol to yield the labeled testosterone (VIII). The reduction of the double bond of (VIII) with Li in liquid ammonia affords the dihydro compound (IX), which is oxidized with Jones oxidant in acetone to provide the labeled androstane-3.17-dione (X). The selective reduction of the 3-oxo group of (X) by means of tri-tert-butoxy lithium aluminum hydride in hot THF gives the labeled 3-beta-hydroxyandrostan-17-one (XI), which is brominated with CuBr2 in refluxing methanol to yield the target alpha-bromo derivative, along with some beta-isomer that is separated by column chromatography

参考文献No.693920
标题:Synthesis of dehydroepiandrosterone sulfatide and 16alpha-halogenated steroids
作者:Abou-Gharbia, M.; Pashko, L.; Schwartz, A.; Swern, D.
来源:J Pharm Sci 1981,70(10),1154
合成路线图解说明:

Epiandrosterone (I) was converted to the oximino ketone (II) by nitrosation with isoamyl nitrite in the presence of potassium tert-butoxide. Reaction of (II) with sodium hypochlorite and ammonia gave rise to the diazo ketone (III), which, upon treatment with HBr, afforded the title 16-alpha-bromo derivative

合成路线图解说明:

Alternatively, the title compound was directly obtained by bromination of epiandrosterone (I) with cupric bromide in refluxing MeOH

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