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【结 构 式】 
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【药物名称】Venritidine hydrochloride, D-16637 【化学名称】(±)-(Z)-N-Methyl-2-nitro-N'-[2-[[5-[(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]furfuryl]thio]ethyl]-1,1-ethenediamine 【CA登记号】93064-63-2 (free base) 【 分 子 式 】C18H27ClN4O3S 【 分 子 量 】414.95789 |
【开发单位】Degussa (Originator) 【药理作用】Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, Histamine H2 Receptor Antagonists |
合成路线1
The Mannich reaction of tricyclo[2.2. 1.0(2,6)]hept-3-ylamine hydrochloride (I) with 2-furanylmethanol (II) and paraformaldehyde (III) in ethanol gives 5-(tricyclo[2.2. 1.0(2,6)]hept-3-ylamino)methyl-2-furanyl methanol (IV). The reaction of compound (IV) with 2 mercaptoethylamine (V) by means of concentrated HCl affords 2 [[[5-[(tricyclo[2.2.1.0(2,6)]hept-3-yl-amino(methyl]-2-furanyl]methyl]thio]etheneamine (VI), which is converted with 1 1-bis(methylthio)-2-nitroethene (VII) in isopropyl alcohol by heating at 70 C to N-[2-[[[5 [(tricyclo[2.2.1.O(2,6)]hept-3-ylamino)methyl]-2-furanyl]methyl]thio]ethyl]-1-(methylthio)-2-nitroetheneamine (VIII). Compound (VIII) is then treated with excess methylamine in ethanol at 0 C, followed by treatment with ethereal HCl to give the desired-N-[2-[[[5 [(tricyclo[2.2. 1.0(2,6)]hept-3-ylamino)methyl]-2 furanyl]methyl]thio]ethyl] N'- methyl-2-nitro-1,1-ethenediaminehydrochloride.
| 【1】 Emig, P.; et al. (Degussa-Huls AG); Novel ethenediamine and guanidine derivatives. DE 3343884 . |
| 【2】 Castaner, J.; Prous, J.; D-16637. Drugs Fut 1986, 11, 1, 14. |
| 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) | 24124 | tricyclo[2.2.1.0(2,6)]hept-3-ylamine | C7H11N | 详情 | 详情 | |
| (II) | 13848 | 2-Furylmethanol; Furfuryl Alcohol | 98-00-0 | C5H6O2 | 详情 | 详情 |
| (IV) | 24126 | [5-[(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]-2-furyl]methanol | C13H17NO2 | 详情 | 详情 | |
| (V) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (VI) | 24128 | N-[(5-[[(2-aminoethyl)sulfanyl]methyl]-2-furyl)methyl]-N-tricyclo[2.2.1.0(2,6)]hept-3-ylamine | C15H22N2OS | 详情 | 详情 | |
| (VII) | 13853 | Methyl 1-(methylsulfanyl)-2-nitrovinyl sulfide; 1,1-Bis(methylthio)-2-nitroethylene; 1,1-Bis(methylsulfanyl)-2-nitroethylene | 13623-94-4 | C4H7NO2S2 | 详情 | 详情 |
| (VIII) | 24130 | N-[(Z)-1-(methylsulfanyl)-2-nitroethenyl]-N-[2-[([5-[(tricyclo[2.2.1.0(2,6)]hept-3-ylamino)methyl]-2-furyl]methyl)sulfanyl]ethyl]amine | C18H25N3O3S2 | 详情 | 详情 |