【结 构 式】 |
【分子编号】11290 【品名】1-Ethyl-6-fluoro-4-oxo-7-piperazino-1,4-dihydro-3-quinolinecarboxylic acid; Norfloxacin 【CA登记号】70458-96-7 |
【 分 子 式 】C16H18FN3O3 【 分 子 量 】319.3357432 【元素组成】C 60.18% H 5.68% F 5.95% N 13.16% O 15.03% |
合成路线1
该中间体在本合成路线中的序号:(I)By acylation of 1-ethyl-6-fluoro-4-oxo-7-piperazine-1,4-dihydroquinoline-3-carboxylic acid (I) with succinic anhydride (II) in refluxing dichloromethane. Acetic acid can also be used as solvent in the acylation.
【1】 Di Schiena, M. (Farmades); Cpds. having antibacterial activity, process for their preparation and pharmaceutical compsns. Containing them. EP 0155006 . |
【2】 Prous, J.; Castaner, J.; NORFLOXACIN SUCCINIL. Drugs Fut 1990, 15, 6, 578. |
合成路线2
该中间体在本合成路线中的序号:(IV)The condensation of trimethoprim (I) with 5-bromoisatin (II) in ethanolic HOAc produced the imine adduct (III). Subsequent condensation with norfloxacin (IV) and formaldehyde yielded the title Mannich base.
【1】 Nath, G.; Pandeya, S.N.; De Clercq, E.; Sriram, D.; Synthesis, antibacterial, antifungal and anti-HIV activities for norfloxacin Mannich bases. Eur J Med Chem 2000, 35, 2, 249. |
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) | 42591 | 5-(3,4,5-trimethoxybenzyl)-2,4-pyrimidinediamine; 2-amino-5-(3,4,5-trimethoxybenzyl)-4-pyrimidinylamine | 738-70-5 | C14H18N4O3 | 详情 | 详情 |
(II) | 42592 | 5-bromo-1H-indole-2,3-dione | 87-48-9 | C8H4BrNO2 | 详情 | 详情 |
(III) | 42593 | 3-[[4-amino-5-(3,4,5-trimethoxybenzyl)-2-pyrimidinyl]imino]-5-bromo-1,3-dihydro-2H-indol-2-one | C22H20BrN5O4 | 详情 | 详情 | |
(IV) | 11290 | 1-Ethyl-6-fluoro-4-oxo-7-piperazino-1,4-dihydro-3-quinolinecarboxylic acid; Norfloxacin | 70458-96-7 | C16H18FN3O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号:(IV)The alkylation of ciprofloxacin (I) with bis(chloromethyl)benzene (II) afforded the monosubstituted adduct (III). This was further condensed with norfloxacin (IV) to yield the title heterodimer compound.
【1】 Grucz, R.G.; Kerns, R.J.; Kaatz, G.W.; Vaka, F.; Rybak, M.J.; Synthesis and antibacterial activity of novel piperazinyl-linked fluoroquinolones. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-565. |
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) | 22103 | 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid | 85721-33-1 | C17H18FN3O3 | 详情 | 详情 |
(II) | 55918 | 1,4-Bis(chloromethyl)benzene; alpha,alpha'-Dichloro-p-xylene; p-Xylylene dichloride | 623-25-6 | C8H8Cl2 | 详情 | 详情 |
(III) | 55919 | 7-{4-[4-(chloromethyl)benzyl]-1-piperazinyl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid | C25H25ClFN3O3 | 详情 | 详情 | |
(IV) | 11290 | 1-Ethyl-6-fluoro-4-oxo-7-piperazino-1,4-dihydro-3-quinolinecarboxylic acid; Norfloxacin | 70458-96-7 | C16H18FN3O3 | 详情 | 详情 |