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【结 构 式】 
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【药物名称】 【化学名称】1-[1-(4-Chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl]ethanone 【CA登记号】66040-38-8 【 分 子 式 】C19H20ClNO3 【 分 子 量 】345.82915 |
【开发单位】Università degli Studi di Catanzaro (Originator), Università degli Studi di Messina (Originator), University of London (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS, AMPA Antagonists |
合成路线1
Condensation between 2-(3,4-dimethoxyphenyl)ethylamine (I) and 4-chlorobenzaldehyde (II) in refluxing toluene affords imine (III). Then, Pictet-Spengler cyclization of imine (III) in the presence of trifluoroacetic acid leads to the tetrahydroisoquinoline (IV). This is further acylated in boiling acetic anhydride to produce the target acetamide.
| 【1】 Gitto, A.; Barreca, M.L.; De Luca, L.; De Sarro, G.; Ferreri, G.; Quartarone, S.; Russo, E.; Constanti, A.; Chimirri, A.; Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. J Med Chem 2003, 46, 1, 197. |
| 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) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (II) | 29029 | 4-chlorobenzaldehyde | 104-88-1 | C7H5ClO | 详情 | 详情 |
| (III) | 65051 | N-[(E)-(4-chlorophenyl)methylidene]-2-(3,4-dimethoxyphenyl)-1-ethanamine; N-[(E)-(4-chlorophenyl)methylidene]-N-(3,4-dimethoxyphenethyl)amine | C17H18ClNO2 | 详情 | 详情 | |
| (IV) | 65052 | 1-(4-chlorophenyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether; 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | C17H18ClNO2 | 详情 | 详情 |
Extended Information