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【结 构 式】 
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【药物名称】 【化学名称】N,N'-[1,3-Propanediylbis[(methylimino)-2,1-ethanediyl]]bis[4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamide] 【CA登记号】214637-59-9 【 分 子 式 】C45H42N6O4 【 分 子 量 】730.87429 |
【开发单位】La Trobe University (Originator), University of Auckland (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA Topoisomerase I Inhibitors, DNA-Intercalating Drugs |
合成路线1
Methyl anthranilate (I) was condensed with chloral hydrate and hydroxylamine to produce the hydroxymino acetamide (II), which was cyclized to the required isatin-7-carboxylic acid (III) in hot concentrated sulfuric acid. The Pfitzinger condensation of isatin (III) with 7-methyl-1-indanone (IV) gave rise to indenoquinoline (V). Ketone (VI) was then obtained by oxidation of (V) with potassium permanganate in the presence of sodium carbonate. Subsequent thermal decarboxylation of diacid (VI) afforded monocarboxylic acid (VII) (1). After activation of acid (VII) as the corresponding imidazolide (VIII) upon treatment with N,N'-carbonyl diimidazole, coupling with tetraamine (IX) furnished the title bisamide.
| 【1】 Finlay, G.J.; Baguley, B.C.; Desneves, J.; Kaye, A.J.; Denny, W.A.; Deady, L.W.; Synthesis and antitumor activity of some indeno[1,2-b]quinoline-based bis carboxamides. Bioorg Med Chem 2000, 8, 5, 977. |
| 【2】 Denny, W.A.; Deady, L.W.; Kaye, A.J. (La Trobe University); Topoisomerase inhibitors. WO 9845272 . |
| 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) | 11161 | methyl 2-aminobenzoate; Methyl anthranilate | 134-20-3 | C8H9NO2 | 详情 | 详情 |
| (II) | 42161 | methyl 2-[[2-(hydroxyimino)acetyl]amino]benzoate | C10H10N2O4 | 详情 | 详情 | |
| (III) | 42162 | 2,3-dioxo-7-indolinecarboxylic acid | C9H5NO4 | 详情 | 详情 | |
| (IV) | 42163 | 7-methyl-1-indanone | C10H10O | 详情 | 详情 | |
| (V) | 42164 | 4-methyl-11H-indeno[1,2-b]quinoline-6,10-dicarboxylic acid | C19H13NO4 | 详情 | 详情 | |
| (VI) | 42165 | 4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6,10-dicarboxylic acid | C19H11NO5 | 详情 | 详情 | |
| (VII) | 42166 | 4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid | C18H11NO3 | 详情 | 详情 | |
| (VIII) | 42167 | 6-(1H-imidazol-1-ylcarbonyl)-4-methyl-11H-indeno[1,2-b]quinolin-11-one | C21H13N3O2 | 详情 | 详情 | |
| (IX) | 42168 | N(1),N(3)-bis(2-aminoethyl)-N(1),N(3)-dimethyl-1,3-propanediamine; N-(2-aminoethyl)-N-[3-[(2-aminoethyl)(methyl)amino]propyl]-N-methylamine | C9H24N4 | 详情 | 详情 |