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【结 构 式】 
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【药物名称】Indanocine, NSC-698666 【化学名称】7-Amino-2-[(E)-(4-hydroxy-3,5-dimethylbenzylidene]-5,6-dimethoxyindan-1-one 【CA登记号】 【 分 子 式 】C20H21NO4 【 分 子 量 】339.39467 |
【开发单位】National Cancer Institute (Originator), University of California, San Diego (Originator) 【药理作用】Oncolytic Drugs, Antimitotic Drugs, Apoptosis Inducers, Microtubule-Stabilizing Agents |
合成路线1
5,6-Dimethoxy-1-indanone (I) was selectively nitrated at position 7 by means of NaNO2 in trifluoroacetic acid. Acid-catalyzed aldol condensation of the resulting nitroindanone (II) with 3,5-dimethyl-4-hydroxybenzaldehyde (III) afforded the E-unsaturated ketone (IV). Finally, reduction of the nitro group of (IV) with either sodium dithionite or zinc dust and AcOH yielded the corresponding amino derivative.
| 【1】 Shih, H.; Carson, D.A.; Deng, L.; Carrer, C.J.; Cottam, H.B.; Adachi, C.J.; Rational design, synthesis and structure-activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones. Bioorg Med Chem Lett 2000, 10, 5, 487. |
| 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) | 13430 | 5,6-Dimethoxy-1-indanone; 2,3-Dihydro-5,6-dimethoxy-1H-inden-1-one | 2107-69-9 | C11H12O3 | 详情 | 详情 |
| (II) | 39984 | 5,6-dimethoxy-7-nitro-1-indanone | C11H11NO5 | 详情 | 详情 | |
| (III) | 39985 | 4-hydroxy-3,5-dimethylbenzaldehyde；3,5-Dimethyl-4-hydroxybenzaldehyde | 2233-18-3 | C9H10O2 | 详情 | 详情 |
| (IV) | 39986 | 2-[(E)-(4-hydroxy-3,5-dimethylphenyl)methylidene]-5,6-dimethoxy-7-nitro-1-indanone | C20H19NO6 | 详情 | 详情 |