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【结 构 式】 
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【药物名称】 【化学名称】N-Isopropylcarbamic acid 5,10-dioxo-5,10-dihydropyrido[3,2-g]quinolin-3-ylmethyl ester 【CA登记号】 【 分 子 式 】C17H15N3O4 【 分 子 量 】325.3268 |
【开发单位】Chungbuk National University (Originator), Konkuk University (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA Topoisomerase II Inhibitors |
合成路线1
The hetero Diels-Alder condensation of quinolinedione (I) with the azabutadiene (II) in the presence of ZnBr2 produced regioselectively the pyridoquinoline (III). Benzylic bromination of (III) using N-bromosuccinimide then gave bromomethyl derivative (IV). Subsequent treatment of (IV) with NaOAc in DMF, followed by hydrolysis of the resulting acetate (V), afforded 3-(hydroxymethyl)pyridoquinoline (VI). This was finally treated with isopropyl isocyanate in the presence of Et3N and dibutyltin diacetate to yield the target carbamate.
| 【1】 Lee, H.; Lee, S.I.; Yang, S.I.; Synthesis and in vitro cytotoxicity of 3-substituted-1,8-diazaanthraquinones produced by Lewis-acid catalyzed hetero Diels-Alder reaction. Bioorg Med Chem Lett 1998, 8, 21, 2991. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 30690 | isopropyl isocyanate; 2-isocyanatopropane | 1795-48-8 | C4H7NO | 详情 | 详情 | |
| (I) | 25759 | 5,8-quinolinedione | C9H5NO2 | 详情 | 详情 | |
| (II) | 25760 | 2-methylacrylaldehyde N,N-dimethylhydrazone | C6H12N2 | 详情 | 详情 | |
| (III) | 25761 | 3-methylpyrido[3,2-g]quinoline-5,10-dione | C13H8N2O2 | 详情 | 详情 | |
| (IV) | 25762 | 3-(bromomethyl)pyrido[3,2-g]quinoline-5,10-dione | C13H7BrN2O2 | 详情 | 详情 | |
| (V) | 25763 | (5,10-dioxo-5,10-dihydropyrido[3,2-g]quinolin-3-yl)methyl acetate | C15H10N2O4 | 详情 | 详情 | |
| (VI) | 25764 | 3-(hydroxymethyl)pyrido[3,2-g]quinoline-5,10-dione | C13H8N2O3 | 详情 | 详情 |