Cystemustine, CMSO2EN2

N'-(2-氯乙基)-N-(2-(甲基磺酰基)乙基)-N'-亚硝基脲Chemical Name: N-(2-Chloroethyl)-N'-[2-(methylsulfonyl)ethyl]-N-nitrosourea
CAS No. 79955-36-5
项目整合开发状态: Phase II
项目研究机构: CNRS (Originator), INSERM (Originator)
合成路线:The reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III),which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV).The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI),which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.
📌 参考资料/链接:
参考文献标题:Novel nitrosourea cpds.Process of preparation.Compsns.based on these cpds.useful in anticancer chemotherapy
文献作者:Godeneche,D.; Imbach,J.-L.; Madelmont,J.-C.; Meyniel,G.; Moreau,M.-F.; Oiry,J.; Parry,D.(CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale))
参考来源:EP 0185020; FR 2562890; JP 1988502269; WO 8504655

📄 详细内容


合成路线:The reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III),which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV).The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI),which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.

参考文献标题:Nitrosoureas compounds,preparation thereof and utilization thereof in anticancerous
文献作者:Madelmont,J.-C.; Godeneche,D.; Moreau,M.-F.; Parry,D.; Meyniel,G.; Oiry,J.; Imbach,J.-L.(CNRS (Centre National de la Recherche Scientifique); INSERM (Institut National de la Sante et de la Recherche Medicale))
参考来源:US 5001158


合成路线:The reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III),which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV).The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI),which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.

参考文献标题:New cysteamin(2-chloroethyl)nitrosoureas.Synthesis and preliminary antitumor results
文献作者:Madelmont,J.C.; Godeneche,D.; Parry,D.; Duprat,J.; Chabard,J.L.; Plagne,R.; Mathe,G.; Meyniel,G.
参考来源:J Med Chem 1985,28(9),1346-50


合成路线:The reaction of 4-nitrophenol (I) with 2-chloroethyl isocyanate (II) in pyridine leads to the activated carbamate (III),which is nitrosated by reacting with nitrosyl chloride in pyridine at -20 C to yield 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (IV).The nitrosated molecule (IV) is reacted with 2-(methylthio)ethylamine (V) in THF at ordinary temperature affording the sulfure urea (VI),which is then oxidized to the sulfonyl compound (VII) by hydrogen peroxide in formic acid at 50 C.
参考文献标题:Cystemustine
文献作者:Madelmont,J.C.
参考来源:Drugs Fut 1994,19(1),27


产品链接: CAS No. 79955-36-5››