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【结 构 式】 
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【药物名称】Unifiram, DM-232 【化学名称】(8aR)-2-(4-Fluorophenylsulfonyl)perhydropyrrolo[1,2-a]pyrazin-6-one 【CA登记号】272786-64-8 (undefined isomer) 【 分 子 式 】C13H15FN2O3S 【 分 子 量 】298.3385 |
【开发单位】Università degli Studi di Firenze (Originator) 【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS |
合成路线1
Horner-Emmons condensation of 1,4-dibenzyl-2-piperazinecarboxaldehyde (I) with phosphonate (II) gave piperazineacrylate (III). Subsequent double bond hydrogenation and hydrogenolysis of the benzyl groups of (III) produced the spontaneous cyclization of the resulting amino ester to furnish the diazabicyclononanone (IV). Finally, condensation of amine (IV) with p-fluorobenzenesulfonyl chloride (V) yielded the title sulfonamide.
| 【1】 Manetti, D.; et al.; Design, synthesis, and preliminary pharmacological evaluation of 1,4-diazabicyclo[4.3.0]nonan-9-ones as a new class of highly potent nootropic agents. J Med Chem 2000, 43, 10, 1969. |
| 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) | 42117 | 1,4-dibenzyl-2-piperazinecarbaldehyde | C19H22N2O | 详情 | 详情 | |
| (II) | 27698 | methyl 2-(diethoxyphosphoryl)acetate | 1067-74-9 | C7H15O5P | 详情 | 详情 |
| (III) | 42118 | methyl (E)-3-(1,4-dibenzyl-2-piperazinyl)-2-propenoate | C22H26N2O2 | 详情 | 详情 | |
| (IV) | 42119 | hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one | C7H12N2O | 详情 | 详情 | |
| (V) | 12292 | 4-Fluorobenzenesulfonyl chloride | 349-88-2 | C6H4ClFO2S | 详情 | 详情 |