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【结 构 式】 
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【药物名称】 【化学名称】5,7-Dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-4H-1-benzopyran-4-one 【CA登记号】34125-75-2 【 分 子 式 】C20H18O4 【 分 子 量 】322.36406 |
【开发单位】INSERM (Originator), Université Claude Bernard Lyon 1 (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS, P-Glycoprotein (MDR-1) Inhibitors |
合成路线1
Alkylation of chrysin (I) with prenyl bromide (II) in the presence of K2CO3 in acetone provided 7-O-(3,3-dimethylallyl)chrysin (III). Claisen rearrangement of (III) in the presence of NaOAc in refluxing Ac2O gave rise to the 8-(1,1-dimethylallyl) flavone (IV) and minor amounts of the desired 8-(3,3-dimethylallyl) analogue (V). Saponification of the mixture of acetate esters, followed by chromatographic separation, furnished the title 8-(3,3-dimethylallyl)chrysin.
| 【1】 Mariotte, A.-M.; Barron, D.; Syntheses of 8-C-(1,1-dimethylallyl) flavones and 3-methyl flavonols. Nat Prod Lett 1994, 4, 1, 21. |
| 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) | 47707 | 5,7-Dihydroxyflavone; Chrysin; Chrysine; 5,7-dihydroxy-2-phenyl-4H-chromen-4-one | 480-40-0 | C15H10O4 | 详情 | 详情 |
| (II) | 12989 | 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene | 870-63-3 | C5H9Br | 详情 | 详情 |
| (III) | 47708 | 5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one | C20H18O4 | 详情 | 详情 | |
| (IV) | 47709 | 5-(acetoxy)-8-(1,1-dimethyl-2-propenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate | C24H22O6 | 详情 | 详情 | |
| (V) | 47710 | 5-(acetoxy)-8-(3-methyl-2-butenyl)-4-oxo-2-phenyl-4H-chromen-7-yl acetate | C24H22O6 | 详情 | 详情 |
合成路线2
In an improved procedure, chrysin (I) was alkylated with prenyl bromide (II) under phase-transfer conditions, and the resulting prenyl ether (III) was subsequently rearranged under microwave irradiation to produce a mixture of the title compound as the major product along with the 6-prenyl (VI) and the 6,8-diprenyl (VII) derivatives, which were separated by column chromatography.
| 【1】 Conseil, G.; Daskiewicz, J.-B.; Bayet, C.; Viornery-Vanier, A.; Dmontet, C.; Di Pietro, A.; Comte, G.; Barron, D.; C-Isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance. J Med Chem 2001, 44, 5, 763. |
| 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) | 47707 | 5,7-Dihydroxyflavone; Chrysin; Chrysine; 5,7-dihydroxy-2-phenyl-4H-chromen-4-one | 480-40-0 | C15H10O4 | 详情 | 详情 |
| (II) | 12989 | 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene | 870-63-3 | C5H9Br | 详情 | 详情 |
| (III) | 47708 | 5-hydroxy-7-[(3-methyl-2-butenyl)oxy]-2-phenyl-4H-chromen-4-one | C20H18O4 | 详情 | 详情 | |
| (VI) | 47711 | 5,7-dihydroxy-6-(3-methyl-2-butenyl)-2-phenyl-4H-chromen-4-one | C20H18O4 | 详情 | 详情 | |
| (VII) | 47712 | 5,7-dihydroxy-6,8-bis(3-methyl-2-butenyl)-2-phenyl-4H-chromen-4-one | C25H26O4 | 详情 | 详情 |