|
【结 构 式】 
|
【药物名称】Curcumin 【化学名称】(E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione 【CA登记号】458-37-7 【 分 子 式 】C21H20O6 【 分 子 量 】368.38995 |
【开发单位】Central Drug Research Institute (Originator) 【药理作用】AIDS Medicines, Alzheimer's Dementia, Treatment of , Antiarthritic Drugs, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Chemopreventive Agents, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, ONCOLYTIC DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Antioxidants, CCND1 Expression Inhibitors, HIV Integrase Inhibitors |
合成路线1
Synthesis of curcumin was first described by Lampe et al. In our laboratory curcumin has been synthesized by condensing vanillin (I) and acetyl acetone (II) in a medium of ethyl acetate using tributylborate as boron complex to avoid Knoevenagel condensation at C-3 of acetyl acetone. Curcumin is isolated from the reaction mixture by acidification and extraction with ethyl acetate. The organic layers are washed until neutral, dried and the solvent is removed. purified by chromatography over silica gel using ether/petroleum ether as the solvent.
合成路线2
The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 2H-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.
| 【1】 Threadgill, M.D.; Parveen, I.; Labelled compounds of interest as antitumour agents - VII. [H-2]- and [C-14]-curcumin. J Label Compd Radiopharm 2000, 43, 9, 883. |
| 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) | 45436 | 4-bromo-2-methoxyphenol | 7368-78-7 | C7H7BrO2 | 详情 | 详情 |
| (II) | 18762 | 1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene | 109-92-2 | C4H8O | 详情 | 详情 |
| (III) | 45437 | 5-bromo-2-(1-ethoxyethoxy)phenyl methyl ether; 4-bromo-1-(1-ethoxyethoxy)-2-methoxybenzene | C11H15BrO3 | 详情 | 详情 | |
| (IV) | 45438 | [4-(1-ethoxyethoxy)-3-methoxyphenyl]lithium | C11H15LiO3 | 详情 | 详情 | |
| (V) | 33491 | Dimethylformamide | 68-12-2 | C3H7NO | 详情 | 详情 |
| (V) | 45439 | dimethylformamide | C3H7NO | 详情 | 详情 | |
| (VI) | 22701 | 4-hydroxy-3-methoxybenzaldehyde | 121-33-5 | C8H8O3 | 详情 | 详情 |
| (VI) | 45440 | 4-hydroxy-3-methoxybenzaldehyde | 21-59-0 | C8H8O3 | 详情 | 详情 |
| (VII) | 11620 | 2,4-Pentanedione;acetylacetone | 123-54-6 | C5H8O2 | 详情 | 详情 |
合成路线3
The protection of 4-bromo-2-methoxyphenol (I) with ethyl vinyl ether (II) and TsOH in dichloromethane gives the ethoxyethyl ether (III), which is treated with n-BuLi in THF to yield the phenyl lithium compound (IV). The reaction of (IV) with 14C-labeled DMF (V), followed by hydrolysis with HCl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (VI), which is finally condensed with pentane-2,4-dione (VII) by means of B2O3 and tetrahydroquinoline in DMF.
| 【1】 Threadgill, M.D.; Parveen, I.; Labelled compounds of interest as antitumour agents - VII. [H-2]- and [C-14]-curcumin. J Label Compd Radiopharm 2000, 43, 9, 883. |
| 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) | 45436 | 4-bromo-2-methoxyphenol | 7368-78-7 | C7H7BrO2 | 详情 | 详情 |
| (II) | 18762 | 1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene | 109-92-2 | C4H8O | 详情 | 详情 |
| (III) | 45437 | 5-bromo-2-(1-ethoxyethoxy)phenyl methyl ether; 4-bromo-1-(1-ethoxyethoxy)-2-methoxybenzene | C11H15BrO3 | 详情 | 详情 | |
| (IV) | 45438 | [4-(1-ethoxyethoxy)-3-methoxyphenyl]lithium | C11H15LiO3 | 详情 | 详情 | |
| (V) | 33491 | Dimethylformamide | 68-12-2 | C3H7NO | 详情 | 详情 |
| (V) | 45441 | dimethylformamide | C3H7NO | 详情 | 详情 | |
| (VI) | 22701 | 4-hydroxy-3-methoxybenzaldehyde | 121-33-5 | C8H8O3 | 详情 | 详情 |
| (VI) | 45442 | 4-hydroxy-3-methoxybenzaldehyde | C8H8O3 | 详情 | 详情 | |
| (VII) | 11620 | 2,4-Pentanedione;acetylacetone | 123-54-6 | C5H8O2 | 详情 | 详情 |