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【结 构 式】 
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【药物名称】 【化学名称】7,8-Dimethoxy-5-methyl-1-phenyl-3H-pyrazolo[3,4-c]isoquinoline 【CA登记号】107879-55-0 【 分 子 式 】C19H17N3O2 【 分 子 量 】319.36624 |
【开发单位】Daiichi Suntory Pharma (Originator) 【药理作用】Antiarthritic Drugs, Oncolytic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, TNF-alpha Production Inhibitors |
合成路线1
Conversion of alpha-benzoyl-homoveratronitrile (I) into benzopyrylium perchlorate derivative (II) is performed by reaction with perchloric acid in acetic anhydride. The desired compound is then obtained by treatment of (II) with hydrazine hydrate in refluxing acetonitrile. Alternatively, the target product can be obtained as follows: Treatment of homoveratronitrile derivative (I) with hydrazine hydrate in refluxing acetic acid yields pyrazole (III), which is then acylated with acetyl chloride (IV) by means of Et3N in refluxing benzene to furnish acetylamino derivative (V). Finally, cyclization is induced by treatment of (V) with perchloric acid in refluxing acetic anhydride/nitromethane.
| 【1】 Nikolyukin, Y.A.; et al.; Synthesis of azolo(5,4-c) isoquinolines. Chem Heterocycl Compd 1990, 26, 914. |
| 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) | 48918 | 2-(3,4-dimethoxyphenyl)-3-oxo-3-phenylpropanenitrile | C17H15NO3 | 详情 | 详情 | |
| (II) | 48919 | 4-cyano-6,7-dimethoxy-1-methyl-3-phenylisochromenium perchlorate | C19H16ClNO7 | 详情 | 详情 | |
| (III) | 48920 | 4-(3,4-dimethoxyphenyl)-3-phenyl-1H-pyrazol-5-amine; 4-(3,4-dimethoxyphenyl)-3-phenyl-1H-pyrazol-5-ylamine | C17H17N3O2 | 详情 | 详情 | |
| (IV) | 19273 | acetyl chloride | 75-36-5 | C2H3ClO | 详情 | 详情 |
| (V) | 48921 | N-[4-(3,4-dimethoxyphenyl)-3-phenyl-1H-pyrazol-5-yl]acetamide | C19H19N3O3 | 详情 | 详情 |