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【结 构 式】 
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【药物名称】Vanidipinedilol 【化学名称】4-[4-[3-(tert-Butylamino)-2-hydroxypropoxy]-3-methoxyphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl diester hydrochloride 【CA登记号】257284-29-0 【 分 子 式 】C25H37ClN2O7 【 分 子 量 】513.03584 |
【开发单位】Kaohsiung Medical College (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, beta-Adrenoceptor Antagonists, Calcium Channel Blockers |
合成路线1
The condensation of vanillin (I) with epichlorohydrin (II) in ethanolic NaOH produced the glycidyl ether (III). Epoxide ring opening in (III) by means of tert-butylamine (IV) in EtOH furnished amino alcohol (V). The title dihydropyridine derivative was then obtained by reaction between aldehyde (V), methyl acetoacetate (VI), ammonia under Hantzsch condensation conditions, and was isolated after conversion to the hydrochloride salt.
| 【1】 Liang, J.-C.; Chen, I.-J.; Tsai, C.-H.; Liou, S.-F.; Wang, C.-S.; Yeh, J.-L.; The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities. Bioorg Med Chem 2002, 10, 3, 719. |
| 【2】 Donovan, S. (Allergan, Inc.); Method for treating a neoplasm. WO 0209743 . |
| 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) | 22701 | 4-hydroxy-3-methoxybenzaldehyde | 121-33-5 | C8H8O3 | 详情 | 详情 |
| (II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (III) | 59599 | 3-methoxy-4-(2-oxiranylmethoxy)benzaldehyde | C11H12O4 | 详情 | 详情 | |
| (IV) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
| (V) | 59600 | 4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methoxybenzaldehyde | C15H23NO4 | 详情 | 详情 | |
| (VI) | 11791 | methyl 3-oxobutanoate; Methyl acetoacetate | 105-45-3 | C5H8O3 | 详情 | 详情 |