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【结 构 式】 
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【药物名称】A-255916 【化学名称】1-Cyclopropyl-7-fluoro-9-methyl-4-oxo-8-(1,2,3,4-tetrahydro-7-isoquinolinyl)-4H-quinolizine-3-carboxylic acid hydrochloride 【CA登记号】 【 分 子 式 】C23H22ClFN2O3 【 分 子 量 】428.89479 |
【开发单位】Abbott (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Quinolizinones |
合成路线1
Bromoisoquinoline (I) was converted into stannane (II) upon treatment with hexabutylditin in the presence of palladium catalyst. Subsequent Stille coupling of (II) with chloroquinolizinone (III) provided adduct (IV). Then, basic hydrolysis of both ethyl ester and trifluoroacetamide groups afforded the target compound, which was finally converted to the hydrochloride salt.
| 【1】 Bui, M.; Nilius, A.; Nan, Y.; Marron, T.; Stone, G.; Baranowski, J.; Shen, L.; Schultz, C.C.; Raney, P.; Snyder, R.; Or, Y.S.; Synthesis and antibacterial activity of C-8 carbon-linked 2-pyridones. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F560. |
| 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) | 33024 | 1-[7-bromo-3,4-dihydro-2(1H)-isoquinolinyl]-2,2,2-trifluoro-1-ethanone | C11H9BrF3NO | 详情 | 详情 | |
| (II) | 38122 | 2,2,2-trifluoro-1-[7-(tributylstannyl)-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone | C23H36F3NOSn | 详情 | 详情 | |
| (III) | 16831 | ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C16H15ClFNO3 | 详情 | 详情 | |
| (IV) | 38123 | ethyl 1-cyclopropyl-7-fluoro-9-methyl-4-oxo-8-[2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydro-7-isoquinolinyl]-4H-quinolizine-3-carboxylate | C27H24F4N2O4 | 详情 | 详情 |
Extended Information