|
【结 构 式】 
|
【药物名称】Arildone, Win-38020 【化学名称】4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-heptanedione 【CA登记号】56219-57-9 【 分 子 式 】C20H29ClO4 【 分 子 量 】368.90473 |
【开发单位】Sanofi-synthélabo (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
Condensation of 2-chloro-4-methoxyphenol (I) with 1,6-dibromohexane (II) by means of K2CO3 in refluxing acetone to give 1-(2-chloro-4-methoxyphenoxy)-6-bromohexane (III), which is converted into the corresponding iodo derivative (IV) by treatment with NaI in refluxing acetone. Finally, (IV) is treated with the lithium salt of 3,5-heptanedione (V) in ether - DMF.
| 【1】 Collins, J.C.; Diana, G.D.; 3,4-Methylenedioxyphenoxy-alkyl diketones and keto-esters. DE 2435378 . |
| 【2】 Diana, G.D.; et al.; Antiviral acticity of some beta-diketones. 2. Aryloxy alkyl diketones. In vitro activity aganist both RNA and DNA viruses. J Med Chem 1977, 20, 6, 757-761. |
| 【3】 Hopkins, S.J.; Castaner, J.; Arildone. Drugs Fut 1978, 3, 1, 12. |
| 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) | 39686 | 2-chloro-4-methoxyphenol | 18113-03-6 | C7H7ClO2 | 详情 | 详情 |
| (II) | 24786 | 1,6-dibromohexane | 629-03-8 | C6H12Br2 | 详情 | 详情 |
| (III) | 39687 | 6-bromohexyl 2-chloro-4-methoxyphenyl ether; 1-[(6-bromohexyl)oxy]-2-chloro-4-methoxybenzene | C13H18BrClO2 | 详情 | 详情 | |
| (IV) | 39688 | 3-chloro-4-[(6-iodohexyl)oxy]phenyl methyl ether; 2-chloro-1-[(6-iodohexyl)oxy]-4-methoxybenzene | C13H18ClIO2 | 详情 | 详情 | |
| (V) | 39689 | 3,5-heptanedione | 7424-54-6 | C7H12O2 | 详情 | 详情 |
合成路线2
Condensation of the lithium salt of 3,5-heptanedione (V) with 1,6-dibromohexane (II) in DMF giving 4-(6-bromohexyl)-3,5-heptanedione (VI), which is then condensed with 2-chloro-4-methoxyphenol (I) by means of NaH in DMF.
| 【1】 Diana, G.D.; et al.; Antiviral acticity of some beta-diketones. 2. Aryloxy alkyl diketones. In vitro activity aganist both RNA and DNA viruses. J Med Chem 1977, 20, 6, 757-761. |
| 【2】 Hopkins, S.J.; Castaner, J.; Arildone. Drugs Fut 1978, 3, 1, 12. |