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【结 构 式】 
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【药物名称】Irloxacin, E-3432 【化学名称】1-Ethyl-6-fluoro-4-oxo-7-(1-pyrrolyl)-1,4-dihydroquinoline-3-carboxylic acid 【CA登记号】91524-15-1 【 分 子 式 】C16H13FN2O3 【 分 子 量 】300.29201 |
【开发单位】Esteve (Originator), Provesan (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Quinolones |
合成路线1
The reduction of 4-fluoro-3-nitroaniline (I) with SnCl2.2H20 in concentrated aqueous HCl gives 4 fluoro-m-phenylenediamine (II), which is condensed with diethyl ethoxymethylenemalonate (III) in refluxing ethanol to afford diethyl 4-fluoro-3-aminoanilinomethylenemalonate (IV). The cyclization of (IV) by means of acetic anhydride in diphenyl oxide at 250 C yields ethyl 7-acetamido-4-hydroxy-6-fluoroquinoline-3-carboxylate (V), which is alkyiated with ethyl bromide and NaOH in refluxing ethanol to give 7-amino-6-fluoro-1-ethyl-1,4 dihydro-4-oxoquinoline-3-carboxylic acid (VI). Finally, this compound is condensed with 2,5-dimethoxytetrahydrofuran (VII) in hot acetic acid.
| 【1】 Esteve Soler, J. (Provesan SA); 7-(1-Pyrrolyl) derivs. of 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids and 1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and their use as antimicrobial agents. EP 0134165; FR 2548664; FR 2559484; US 4552882 . |
| 【2】 Prous, J.; Castaner, J.; Irloxafin. Drugs Fut 1986, 11, 10, 839. |
| 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) | 24710 | 4-fluoro-3-nitroaniline | 364-76-1 | C6H5FN2O2 | 详情 | 详情 |
| (II) | 24711 | 3-amino-4-fluorophenylamine | C6H7FN2 | 详情 | 详情 | |
| (III) | 14088 | Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate | 87-13-8 | C10H16O5 | 详情 | 详情 |
| (IV) | 24713 | diethyl 2-[(3-amino-4-fluoroanilino)methylene]malonate | C14H17FN2O4 | 详情 | 详情 | |
| (V) | 24714 | ethyl 7-(acetamido)-6-fluoro-4-hydroxy-3-quinolinecarboxylate | C14H13FN2O4 | 详情 | 详情 | |
| (VI) | 24715 | 7-amino-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid | C12H11FN2O3 | 详情 | 详情 | |
| (VII) | 12132 | 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether | 696-59-3 | C6H12O3 | 详情 | 详情 |