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【结 构 式】 
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【药物名称】 【化学名称】N-[2-(Dimethylamino)ethyl]-2-methyl-7-oxo-7H-naphtho[1,2,3-de]quinoline-11-carboxamide 【CA登记号】 【 分 子 式 】C22H21N3O2 【 分 子 量 】359.43157 |
【开发单位】La Trobe University (Originator), University of Auckland (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
Nitration of anthraquinone-1-carboxylic acid (I) produced a mixture of 5-nitro (II) and 8-nitro (III) anthraquinones from which the desired 8-nitro isomer (III) was separated by fractional crystallization from ethanol and further purified by washing with toluene. Reduction of the nitro group of (III) with aqueous sodium sulfide gave 8-aminoanthraquinone-1-carboxylic acid (IV). Condensation of (IV) with acetone in the presence of NaOH furnished the dibenzoisoquinolinone system (V). After activation of the carboxylate group of (V) as the imidazolide (VI) upon treatment with carbonyldiimidazole, its coupling with N,N-dimethylethylenediamine (VII) afforded the target amide.
| 【1】 Bu, X.; et al.; Synthesis and cytotoxic activity of 7-oxo-7H-dibenz [f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J Med Chem 2001, 44, 12, 2004. |
| 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) | 50964 | 9,10-dioxo-9,10-dihydro-1-anthracenecarboxylic acid | C15H8O4 | 详情 | 详情 | |
| (II) | 50965 | 5-nitro-9,10-dioxo-9,10-dihydro-1-anthracenecarboxylic acid | C15H7NO6 | 详情 | 详情 | |
| (III) | 50966 | 8-nitro-9,10-dioxo-9,10-dihydro-1-anthracenecarboxylic acid | C15H7NO6 | 详情 | 详情 | |
| (IV) | 50967 | 8-amino-9,10-dioxo-9,10-dihydro-1-anthracenecarboxylic acid | C15H9NO4 | 详情 | 详情 | |
| (V) | 50968 | 2-methyl-7-oxo-7H-naphtho[1,2,3-de]quinoline-11-carboxylic acid | C18H11NO3 | 详情 | 详情 | |
| (VI) | 50969 | 11-(1H-imidazol-1-ylcarbonyl)-2-methyl-7H-naphtho[1,2,3-de]quinolin-7-one | C21H13N3O2 | 详情 | 详情 | |
| (VII) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |