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【结 构 式】 
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【药物名称】 【化学名称】(Tricarbonyl)[(1,2,3,4,5-eta)-3-[1-(4-hydroxyphenyl)-1-[4-[4-(dimethylamino)butoxy]phenyl]-1-buten-2-yl]-2,4-cyclopentadien-1-yl]rhenium 【CA登记号】339320-31-9 ((E)-isomer), 339320-29-5 ((Z)-isomer) 【 分 子 式 】C30H32NO5Re 【 分 子 量 】672.79324 |
【开发单位】Ecole Nationale Supérieure Chimie Paris (Originator), Institut Jules Bordet (Originator) 【药理作用】Breast Cancer Therapy, Oncolytic Drugs, Radiation Therapy, Antiestrogens |
合成路线1
4,4'-Dihydroxybenzophenone (I) is condensed with 1,4-dibromobutane (II) by means of KH in THF/DMF to afford monoalkylated compound (III), which is then subjected to a McMurry cross-coupling reaction with the organometallic compound (IV) in refluxing THF in the presence of TiCl4 and Zn to provide the isomeric mixture (V). Finally, bromo compound (V) is converted into the target product by first heating with dimethylamine (HNMe2) in MeOH followed by isomer separation by means of preparative HPLC chromatography.
| 【1】 Jaouen, G.; et al.; First anti-oestrogen in the cyclopentadienyl rhenium tricarbonyl series. Synthesis and study of antiproliferative effects. Chem Commun (London) 2001, 4, 383. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Z)-(V) | 46772 | C28H29BrO5Re | 详情 | 详情 | ||
| (E)-(V) | 46773 | C28H29BrO5Re | 详情 | 详情 | ||
| (I) | 20637 | bis(4-hydroxyphenyl)methanone | 611-99-4 | C13H10O3 | 详情 | 详情 |
| (II) | 11883 | 1,4-Dibromobutane; 1,4-Butylene bromide | 110-52-1 | C4H8Br2 | 详情 | 详情 |
| (III) | 46770 | [4-(4-bromobutoxy)phenyl](4-hydroxyphenyl)methanone | C17H17BrO3 | 详情 | 详情 | |
| (IV) | 46771 | C11H12O4Re | 详情 | 详情 |