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【结 构 式】

【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
Extended Information