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【结 构 式】 
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【药物名称】NIP-142 【化学名称】N-[4(S)-(Cyclopropylamino)-3(R)-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-1-benzopyran-6-yl]-2-(4-methoxyphenyl)acetamide 【CA登记号】203002-75-9, 203002-58-8 (trans-isomer) 【 分 子 式 】C23H27N3O6 【 分 子 量 】441.48814 |
【开发单位】Nissan Chemical (Originator) 【药理作用】Antiarrhythmic Drugs, CARDIOVASCULAR DRUGS, K(V)1.5 Channel Blockers, L-Type Calcium Channel Blockers, T-Type Calcium Channel Blockers |
合成路线1
The condensation of 2,2-dimethyl-7-nitro-2H-1-benzopyran-6-amine (I) with 4-methoxyphenylacetyl chloride (II) by means of triethylmaine in chloroform gives the corresponding amide (III), which is regioselectively epoxidized with ClONa and a chiral manganese catalyst yielding the epoxide (IV). Finally, this compound is treated with cyclopropylamine in refluxing ethanol.
| 【1】 Ohrai, K.; Sato, M.; Yanagihara, K.; Tanikawa, K.; Yamashita, T.; Shigeta, Y.; Structure-activity relationships and pharmacological activities of benzopyran derivatives with selective bradycardic and anti-fibrillatory effects. Symp Med Chem 1998, Abst 1-P-29. |
| 【2】 Tanikawa, K.; Ohrai, K.; Sato, M.; Yamashita, T.; Yanagihara, K. (Nissan Chemical Industry, Ltd.); Chroman derivs.. EP 0934296; JP 1998087650; US 6066631; WO 9804542 . |
| 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) | 26757 | 2,2-dimethyl-7-nitro-2H-chromen-6-amine | C11H12N2O3 | 详情 | 详情 | |
| (II) | 26758 | 2-(4-methoxyphenyl)acetyl chloride | 4693-91-8 | C9H9ClO2 | 详情 | 详情 |
| (III) | 26759 | N-(2,2-dimethyl-7-nitro-2H-chromen-6-yl)-2-(4-methoxyphenyl)acetamide | C20H20N2O5 | 详情 | 详情 | |
| (IV) | 26760 | N-[(1aR,7bR)-2,2-dimethyl-5-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-6-yl]-2-(4-methoxyphenyl)acetamide | C20H20N2O6 | 详情 | 详情 | |
| (V) | 12263 | Cyclopropylamine; Cyclopropanamine | 765-30-0 | C3H7N | 详情 | 详情 |