网站主页>>>
项目整合精选>>>
项目整合精选>>>Zileuton, CTI-02, ABT-077, A-64077, Zyflo Filmtab , Zyflo, Leutrol
Zileuton, CTI-02, ABT-077, A-64077, Zyflo Filmtab , Zyflo, Leutrol
齐留通Chemical Name: (?-N-Hydroxy-N-[1-(benzothiophen-2-yl)ethyl]urea; (?-N-Hydroxy-N-[1-(benzo[b]thien-2-yl)ethyl]urea; (?-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea
CAS No. 111406-87-2
项目整合开发状态: Registered-1996
项目研究机构: Abbott (Originator), National Cancer Institute (Not Determined), Critical Therapeutics (Licensee), SkyePharma (Formulation)
合成路线:The synthesis of zileuton involved conventional synthetic procedures starting with 2-acetylbenzo[b]thiophene.Treatment of a solution of 2-acetylbenzo[b]thiophene (I) in ethanol/pyridine (1:1) with hydroxylamine hydrochloride at room temperature provided the corresponding oxime (II).To the oxime (II) dissolved in ethanol was added borane:pyridine complex followed by the dropwise addition of 20% HCl in ethanol to provide the hydroxylamine (III),isolated by extraction after neutralization of the acidic mixture.The hydroxylamine (III) was converted to zileuton by either heating with trimethylsilylisocyanate in dioxane or by reacting with KOCN and aqueous HCl.
📌 参考资料/链接：
参考文献标题:Indole,benzofuran,benzothiophene containing lipoxygenease inhibiting compounds
文献作者:Summers,J.B.Jr.; Gunn,B.P.; Brooks,D.W.(Abbott Laboratories Inc.)
参考来源:EP 0279263; JP 1988264456; US 4873259
📄 详细内容
合成路线:The synthesis of zileuton involved conventional synthetic procedures starting with 2-acetylbenzo[b]thiophene.Treatment of a solution of 2-acetylbenzo[b]thiophene (I) in ethanol/pyridine (1:1) with hydroxylamine hydrochloride at room temperature provided the corresponding oxime (II).To the oxime (II) dissolved in ethanol was added borane:pyridine complex followed by the dropwise addition of 20% HCl in ethanol to provide the hydroxylamine (III),isolated by extraction after neutralization of the acidic mixture.The hydroxylamine (III) was converted to zileuton by either heating with trimethylsilylisocyanate in dioxane or by reacting with KOCN and aqueous HCl.
参考文献标题:Zileuton
文献作者:Brooks,D.W.; Rubin,P.D.; Carter,G.W.; Dube,L.M.; Bell,R.L.
参考来源:Drugs Fut 1993,18(7),616
合成路线:A new efficient synthesis of 2-acetylbenzothiophene (I),the key starting material for the previously reported synthesis of zileuton,has been described:Thiophenol (II) is dilithiated with butyllithium and tetramethylethylenediamine in cyclohexane to compound (III),which is then cyclized by successive treatments with DMF and chloroacetone (IV) in THF to afford (I) in high yield.
参考文献标题:Synthesis of the 5-lipoxygenase inhibitor zileuton from thiophenol
文献作者:Brooks,D.W.; Basha,A.
参考来源:J Org Chem 1993,58(5),1293
产品链接: CAS No. 111406-87-2››