Sinitrodil, ITF-296
西硝地尔Chemical Name: 3-[2-(Nitrooxy)ethyl]-2H-1,3-benzoxazin-4(3H)-one
CAS No. 143248-63-9
项目整合开发状态: Phase II
项目研究机构: Italfarmaco (Originator)
合成路线:Sinitrodil (ITF-296) is obtained in four main steps.The reaction of methyl 2-hydroxybenzoate (I) with ethanolamine gives 2-hydroxy-N-(2-hydroxyethyl)benzamide (II),which is converted to 3-(2-hydroxyethyl)-2H-1,3-benzoxazin-4(3H)-one (III) by cyclization with paraformaldehyde under acidic conditions.Treatment of compound (III) with thionyl chloride gives the chloro derivative (IV),which is converted to ITF-296 by reaction with silver nitrate in refluxing acetonitrile.
📌 参考资料/链接：
参考文献标题:Synthesis and cardiovascular activity of 3-nitrooxyalkyl-2,3-dihydro-4H-1,3-benzoxazin-4-ones,a novel class of nitrate esters
文献作者:Levi,S.; Benedini,F.; Bertolini,G.; et al.
参考来源:12th Int Symp Med Chem (Sept 13-17,Basel) 1992,Abst P152C
📄 详细内容
合成路线:Sinitrodil (ITF-296) is obtained in four main steps.The reaction of methyl 2-hydroxybenzoate (I) with ethanolamine gives 2-hydroxy-N-(2-hydroxyethyl)benzamide (II),which is converted to 3-(2-hydroxyethyl)-2H-1,3-benzoxazin-4(3H)-one (III) by cyclization with paraformaldehyde under acidic conditions.Treatment of compound (III) with thionyl chloride gives the chloro derivative (IV),which is converted to ITF-296 by reaction with silver nitrate in refluxing acetonitrile.
参考文献标题:New antianginal nitro-esters with reduced hypotensive activity.Synthesis and pharmacological evaluation of 3-nitrooxyalkyl-2H-1,3-benzoxazin-4(3H)-4-ones
文献作者:Benedini,F.; Bertolini,G.; Cereda,R.; Dona,G.; Gromo,G.; Levi,S.; Mizrahi,J.; Sala,A.
参考来源:J Med Chem 1995,38(1),130-6
合成路线:Sinitrodil (ITF-296) is obtained in four main steps.The reaction of methyl 2-hydroxybenzoate (I) with ethanolamine gives 2-hydroxy-N-(2-hydroxyethyl)benzamide (II),which is converted to 3-(2-hydroxyethyl)-2H-1,3-benzoxazin-4(3H)-one (III) by cyclization with paraformaldehyde under acidic conditions.Treatment of compound (III) with thionyl chloride gives the chloro derivative (IV),which is converted to ITF-296 by reaction with silver nitrate in refluxing acetonitrile.
参考文献标题:Sinitrodil
文献作者:Cereda,R.; Bertolini,G.; Gromo,G.; Mizrahi,J.; Monzani,M.V.; Sala,A.; Sardina,M.; Bergamaschi,M.
参考来源:Drugs Fut 1997,22(3),242
产品链接: CAS No. 143248-63-9››