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【结 构 式】 
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【药物名称】 【化学名称】Thieno[2,3-h]quinolin-2(1H)-one 【CA登记号】 【 分 子 式 】C11H7NOS 【 分 子 量 】201.24854 |
【开发单位】Università degli Studi di Genova (Originator), Università degli Studi di Padova (Originator) 【药理作用】ONCOLYTIC DRUGS, Photosensitizers, Radiation Therapy |
合成路线1
Enamino ketone (II) was synthesized by treatment of benzothiophenone (I) with dimethylformamide dimethylacetal. Condensation of (II) with methyl cyanoacetate (III) led to the pyridone-fused tricyclic system (IV), which was further aromatized to (V) using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Ester group hydrolysis in (V) under acidic conditions afforded acid (VI). This was finally decarboxylated in refluxing quinoline in the presence of copper powder.
| 【1】 Fossa, P.; et al.; Novel angular furo and thieno-quinolinones: Synthesis and preliminary photobiological studies. Bioorg Med Chem 2002, 10, 3, 743. |
| 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) | 11045 | 6,7-Dihydro-1-benzothiophen-4(5H)-one; 4-Keto-4,5,6,7-tetrahydrothianaphthene; Tetrahydrobenzo(b)thiophene-4-one | 13414-95-4 | C8H8OS | 详情 | 详情 |
| (II) | 56091 | 5-[(E)-(dimethylamino)methylidene]-6,7-dihydro-1-benzothiophen-4(5H)-one | C11H13NOS | 详情 | 详情 | |
| (III) | 34458 | Cyanoacetic acid methyl ester; methyl 2-cyanoacetate | 105-34-0 | C4H5NO2 | 详情 | 详情 |
| (IV) | 56092 | methyl 2-oxo-1,2,5,6-tetrahydrothieno[2,3-h]quinoline-3-carboxylate | C13H11NO3S | 详情 | 详情 | |
| (V) | 56093 | methyl 2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylate | C13H9NO3S | 详情 | 详情 | |
| (VI) | 56094 | 2-oxo-1,2-dihydrothieno[2,3-h]quinoline-3-carboxylic acid | C12H7NO3S | 详情 | 详情 |
Extended Information