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【结 构 式】 
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【药物名称】 【化学名称】1-(4-Chlorophenyl)-3-[2-(diethylaminoethyl)amino]-6-hydroxy-2(Z)-hexen-1-one 【CA登记号】 【 分 子 式 】C18H27ClN2O2 【 分 子 量 】338.88109 |
【开发单位】Central Drug Research Institute (Originator) 【药理作用】Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Lipoprotein Disorders, Treatment of , METABOLIC DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Free Radical Scavengers, HDL-Cholesterol Increasing Agents, LDL Antioxidants, Lipid Lowering Agents |
合成路线1
Acetophenone (I) is condensed with gamma-butyrolactone (II) in the presence of NaOMe to afford compound (III), which is finally treated with BF3·Et2O and amine (IV) in dichloromethane/ether. Alternatively, the target compound can be synthesized by regioselective bromination of (III) with PBr3 in dichloromethane to yield bromo derivative (V) followed by heating with primary amine (IV) in MeOH. (Under forceful conditions (V) can be converted into intermediate (VI), which by heating in MeOH in the presence of primary amine (IV) can also lead to the desired product).
| 【1】 Batra, S.; et al.; Syntheses and biological evaluation of 3-substituted amino-1-aryl-6-hydroxy-hex-2-ene-1-ones as antioxidant and hypolipidemic agents. Bioorg Med Chem 2000, 8, 8, 2195. |
| 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) | 12685 | 4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone | 99-91-2 | C8H7ClO | 详情 | 详情 |
| (II) | 20576 | dihydro-2(3H)-furanone | 96-48-0 | C4H6O2 | 详情 | 详情 |
| (III) | 45873 | (Z)-1-(4-chlorophenyl)-3,6-dihydroxy-2-hexen-1-one | C12H13ClO3 | 详情 | 详情 | |
| (IV) | 12420 | N-(2-Aminoethyl)-N,N-diethylamine; N,N-Diethylethylene-diamine; N(1),N(1)-Diethyl-1,2-ethanediamine | 100-36-7 | C6H16N2 | 详情 | 详情 |
| (V) | 45874 | (Z)-6-bromo-1-(4-chlorophenyl)-3-hydroxy-2-hexen-1-one | C12H12BrClO2 | 详情 | 详情 | |
| (VI) | 45875 | 1-(4-chlorophenyl)-2-dihydro-2(3H)-furanylidene-1-ethanone | C12H11ClO2 | 详情 | 详情 |