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【结 构 式】 
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【药物名称】Stiripentol, BCX-2600, Diacomit 【化学名称】4,4-Dimethyl-1-[(3,4-methylenedioxy)phenyl]-1-penten-3-ol 【CA登记号】49763-96-4 【 分 子 式 】C14H18O3 【 分 子 量 】234.29776 |
【开发单位】Biocodex (Orphan Drug), Biocodex (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS, GABA Aminotransferase Inhibitors, GABA Reuptake Inhibitors |
合成路线1
The synthesis of [14]-labeled stiripentol has been published: The reaction of 3,4-methylenedioxybromobenzene (I) with 14CO2 by means of butyllithium in ether gives 3,4-methylenedioxybenzoic acid (II), which is reduced with LiAlH4 to the corresponding benzyl alcohol (III). Oxidation of (III) with CrO3-pyridine affords the aldehyde (IV), which is condensed with methyl tert-butyl ketone (V) by means of NaOH in refluxing ethanol to give the labeled pentanone (VI). Finally, this compound is reduced to [14C]-labeled stiripentol with NaBH4 in methanol.
| 【1】 Lepage, F. Veyre, A.; Madelmont, J.C.; Labarre, P.; Maurizis, J.C.; Rapp, M.; Dupuy, J.M.; Labelling by 14C and 3H of 4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-1-pentene-3-ol or stiripentol. J Label Compd Radiopharm 1992, 31, 11, 961. |
| 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) | 10124 | 5-Bromo-1,3-benzodioxole; 4-Bromo-1,2-(methylenedioxy)benzene | 2635-13-4 | C7H5BrO2 | 详情 | 详情 |
| (II) | 10125 | 1,3-Benzodioxole-5-carboxylic acid | 94-53-1 | C8H6O4 | 详情 | 详情 |
| (II) | 44584 | 1,3-benzodioxole-5-carboxylic acid | C8H6O4 | 详情 | 详情 | |
| (III) | 10126 | 1,3-Benzodioxol-5-ylmethanol; Helioalcohol | 495-76-1 | C8H8O3 | 详情 | 详情 |
| (III) | 44585 | 1,3-benzodioxol-5-ylmethanol | C8H8O3 | 详情 | 详情 | |
| (IV) | 10127 | 1,3-Benzodioxole-5-carbaldehyde; Heliotropine | 120-57-0 | C8H6O3 | 详情 | 详情 |
| (IV) | 44586 | 1,3-benzodioxole-5-carbaldehyde | C8H6O3 | 详情 | 详情 | |
| (V) | 10128 | 3,3-Dimethyl-2-butanone; Pinacolin | 75-97-8 | C6H12O | 详情 | 详情 |
| (VI) | 10129 | (E)-1-(1,3-Benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-one | C14H16O3 | 详情 | 详情 | |
| (VI) | 44587 | (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-one | C14H16O3 | 详情 | 详情 |
合成路线2
The condensation of 3,4-methylenedioxybenzaldehyde (I) with 3,3-dimethyl-2-butanone (II) by means of NaOH in ethanol-water gives 4,4-dimethyl-1-[(3,4-methylenedioxy)phenyl]-1-penten-3-one (III), which is reduced with NaBH4 in methanol.
| 【1】 Vallet, F.M.J.; US 3910959 . |
| 【2】 Astoin, J.; et al.; Action of new ethylenic alcohols on the central nervous system. Eur J Med Chem - Chim Ther 1978, 13, 1, 41-47. |
| 【3】 Castaner, J.; Hillier, K.; Stiripentol. Drugs Fut 1980, 5, 8, 413. |