Tauromustine, TCNU, LS-2667, Tauricyt, -Drug Synthesis Database

【结构式】

【药物名称】Tauromustine, TCNU, LS-2667, Tauricyt

【化学名称】1-(2-Chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosurea

【CA登记号】85977-49-7

【分子式】C₇H₁₅ClN₄O₄S

【分子量】286.739

【开发单位】Leo (Originator)

【药理作用】Oncolytic Drugs, DNA-Damaging Drugs

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

1) N,N-Dimethyl-2-aminoethanesulfonamide (I) is condensed with 2-chloroethyl isocyanate (II) by means of triethylamine in CHCl3 giving 1-(2-chloroethyl)- isocyanate (II) by means of triethylamine in CHCl3 giving 1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]urea (III), which is nitrosated with NaNO3, N2O4 or NOCl in acetic acid-acetic anhydride.

参考文献中间体

【1】 Carlsson, J.-I.; Jensen, P.H.G.; Stamvik, A.R. (Leo Pharma AB); N-nitroso compounds and compositions containing such compounds. EP 0106123; JP 59073562; US 4613695 .
【2】 Prous, J.; Castaner, J.; Tauromustine. Drugs Fut 1986, 11, 7, 585.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24457	3-amino-N,N-dimethyl-1-propanesulfonamide		C₅H₁₄N₂O₂S	详情	详情
(II)	11237	1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate	1943-83-5	C₃H₄ClNO	详情	详情

合成路线2

2) By condensation of (I) with N-(2-chloroethyl)-N-nitrosocarbamoyl hydrazide (IV) in ethanol with triethylamine as catalyst.

参考文献中间体

【1】 Carlsson, J.-I.; Jensen, P.H.G.; Stamvik, A.R. (Leo Pharma AB); N-nitroso compounds and compositions containing such compounds. EP 0106123; JP 59073562; US 4613695 .
【2】 Prous, J.; Castaner, J.; Tauromustine. Drugs Fut 1986, 11, 7, 585.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24457	3-amino-N,N-dimethyl-1-propanesulfonamide		C₅H₁₄N₂O₂S	详情	详情
(IV)	24460	1-(2-chloroethyl)-2-oxo-1-hydrazinecarbonyl azide		C₃H₄ClN₅O₂	详情	详情

合成路线3

3) By condensation of (I) with 1-[N-(2-chloroethyl)-N-nitrosocarbamoyloxy]pyrrolidine-2,5-dione (V) in methanol with triethylamine as catalyst.

参考文献中间体

【1】 Carlsson, J.-I.; Jensen, P.H.G.; Stamvik, A.R. (Leo Pharma AB); N-nitroso compounds and compositions containing such compounds. EP 0106123; JP 59073562; US 4613695 .
【2】 Prous, J.; Castaner, J.; Tauromustine. Drugs Fut 1986, 11, 7, 585.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24457	3-amino-N,N-dimethyl-1-propanesulfonamide		C₅H₁₄N₂O₂S	详情	详情
(V)	24462	1-([[1-(2-chloroethyl)-2-oxohydrazino]carbonyl]oxy)pyrrolidine		C₇H₁₂ClN₃O₃	详情	详情

合成路线4

4) By condensation of (I) with 4-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (VI) in methanol with triethylamine as before.

参考文献中间体

【1】 Carlsson, J.-I.; Jensen, P.H.G.; Stamvik, A.R. (Leo Pharma AB); N-nitroso compounds and compositions containing such compounds. EP 0106123; JP 59073562; US 4613695 .
【2】 Prous, J.; Castaner, J.; Tauromustine. Drugs Fut 1986, 11, 7, 585.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24457	3-amino-N,N-dimethyl-1-propanesulfonamide		C₅H₁₄N₂O₂S	详情	详情
(VI)	11239	4-nitrophenyl 1-(2-chloroethyl)-2-oxo-1-hydrazinecarboxylate		C₉H₈ClN₃O₅	详情	详情

Extended Information