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【结 构 式】 
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【药物名称】Histaprodifen 【化学名称】2-[2-(3,3-Diphenylpropyl)-1H-imidazol-4-yl]-1-ethanamine 【CA登记号】 【 分 子 式 】C20H23N3 【 分 子 量 】305.42641 |
【开发单位】Freie Universität Berlin (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Histamine H1 Agonists |
合成路线1
3,3-Diphenylpropionic acid (I) was treated with SOCl2 to give acid chloride (II) and then converted to amide (III) using liquid ammonia. Dehydration of (III) with P2O5 led to diphenylpropionitrile (IV), which was treated with ammonia in methanol to afford the iminoester (V). The condensation of (V) with 2-oxo-4-phthalimido-1-butyl acetate (VI) in liquid ammonia furnished imidazole (VII). Finally, deprotection of the phthaloyl group of (VII) with methanolic hydrazine afforded the title compound.
| 【1】 Schunack, W.; Detert, H.; Pertz, H.H.; Kramer, K.; ter Laak, A.M.; Kühne, RF.; Elz, S.; Histaprofidens: Synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists. J Med Chem 2000, 43, 6, 1071. |
| 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) | 36717 | 3,3-diphenylpropionic acid | 606-83-7 | C15H14O2 | 详情 | 详情 |
| (II) | 36718 | 3,3-diphenylpropanoyl chloride | C15H13ClO | 详情 | 详情 | |
| (III) | 36719 | 3,3-diphenylpropanamide | C15H15NO | 详情 | 详情 | |
| (IV) | 36720 | 3,3-diphenylpropanenitrile | 2286-54-6 | C15H13N | 详情 | 详情 |
| (V) | 36721 | methyl 3,3-diphenylpropanimidoate | C16H17NO | 详情 | 详情 | |
| (VI) | 36725 | 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxobutyl acetate | C14H13NO5 | 详情 | 详情 | |
| (VII) | 36726 | 2-[2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl]-1H-isoindole-1,3(2H)-dione | C28H25N3O2 | 详情 | 详情 |