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【结 构 式】 
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【分子编号】25759 【品名】5,8-quinolinedione 【CA登记号】 |
【 分 子 式 】C9H5NO2 【 分 子 量 】159.14424 【元素组成】C 67.93% H 3.17% N 8.8% O 20.11% |
合成路线1
该中间体在本合成路线中的序号：(I)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 |
合成路线2
该中间体在本合成路线中的序号：(II)The cyclization of quinoline-5,8-dione (I) with dimethylhydrazone (II) in refluxing acetic anhydride gives the pyridoquinolinedione (III), which is finally cyclized to the target pentacyclic ketone by means of TFA in refluxing dichloromethane.
| 【1】 Bastide, J.; Darro, F.; Bontemps-Subielos, N.; Frydman, A.; Decaestecker, C.; Delfourne, E.; Kiss, R.; Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid. J Med Chem 2001, 44, 20, 3275. |
| 【2】 Kiss, R.; Bontemps-Subielos, N.; Frydman, A.; Darro, F.; Bastide, J.; Deflourne, E. (Laboratoires L. Lafon); Pharmaceutical compsn. based on polyaromatic cpds.. FR 2790954; WO 0055160 . |
| 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) | 48817 | N-(2-[(E)-3-[(E)-2,2-dimethylhydrazono]-1-propenyl]phenyl)-2,2,2-trifluoroacetamide | C13H14F3N3O | 详情 | 详情 | |
| (II) | 25759 | 5,8-quinolinedione | C9H5NO2 | 详情 | 详情 | |
| (III) | 48818 | N-[2-(5,10-dioxo-5,10-dihydropyrido[3,2-g]quinolin-4-yl)phenyl]-2,2,2-trifluoroacetamide | C20H10F3N3O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)The cyclization of dimethylhydrazone (I) with quinoline-5,8-dione (II) in refluxing acetic anhydride gives the target pyridoquinolinedione.
| 【1】 Bastide, J.; Darro, F.; Bontemps-Subielos, N.; Frydman, A.; Decaestecker, C.; Delfourne, E.; Kiss, R.; Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid. J Med Chem 2001, 44, 20, 3275. |
| 【2】 Kiss, R.; Bontemps-Subielos, N.; Frydman, A.; Darro, F.; Bastide, J.; Deflourne, E. (Laboratoires L. Lafon); Pharmaceutical compsn. based on polyaromatic cpds.. FR 2790954; WO 0055160 . |