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【结 构 式】 
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【药物名称】FT-Alz 【化学名称】5-(2,6-Dideoxy-2-fluoro-alpha-L-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione 【CA登记号】 【 分 子 式 】C23H18FNO7 【 分 子 量 】439.40081 |
【开发单位】Institute of Bioorganic Chemistry (Originator), Keio University (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, Oncolytic Drugs, Apoptosis Inducers, DNA Topoisomerase II Inhibitors |
合成路线1
Coupling of alizarin blue (I) with the pyranosyl bromide (II) under Koenigs-Knorr conditions in the presence of HgO and HgBr2 afforded the target 5-talopyranoside derivative (III) along with minor amounts of the 5,6-bis-talopyranoside, which were separated by preparative thin layer chromatography. Deacetylation of (III) using NaOMe in MeOH-THF then gave the title compound.
| 【1】 Tsuchiya, T.; Takagi, Y.; Yamada, H.; Preparation of 5-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione (FT-Alz), a new-type, potentially antitumor substance with various biological activities. Bioorg Med Chem Lett 2000, 10, 3, 203. |
| 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) | 46979 | 5,6-dihydroxynaphtho[2,3-f]quinoline-7,12-dione | C17H9NO4 | 详情 | 详情 | |
| (II) | 16222 | (2S,3S,4R,5R,6S)-3-(acetoxy)-6-bromo-5-fluoro-2-methyltetrahydro-2H-pyran-4-yl acetate | C10H14BrFO5 | 详情 | 详情 | |
| (III) | 46980 | (2S,3R,4R,5R,6S)-3-(acetoxy)-5-fluoro-6-[(6-hydroxy-7,12-dioxo-7,12-dihydronaphtho[2,3-f]quinolin-5-yl)oxy]-2-methyltetrahydro-2H-pyran-4-yl acetate | C27H22FNO9 | 详情 | 详情 |