|
【结 构 式】 
|
【药物名称】 【化学名称】1,10-Diazabicyclo[8.3.1]tetradeca-5,12-diene-3,7-diyne-11,14-dione 【CA登记号】 【 分 子 式 】C12H8N2O2 【 分 子 量 】212.20976 |
【开发单位】Academia Sinica (Originator), University of Alberta (Originator) 【药理作用】Antineoplastic Enhancing Agents, Modulators of the Therapeutic Activity of Antineoplastic Agents, ONCOLYTIC DRUGS, Enediynes |
合成路线1
Alkylation of uracil (I) with propargyl bromide (II) in the presence of DBU affords the N1-alkylated product (III). Palladium-catalyzed coupling of the terminal alkyne (III) with cis-1,2-dichloroethene (IV) furnishes the chlorovinyl adduct (V). Subsequent alkylation at the N3-position of (V) with propargyl bromide (II) and DBU leads to the open-chain enediyne (VI). This is finally cyclized to the target bicyclic compound in the presence of Pd(PPh3)4, CuI and butylamine.
| 【1】 Hakimelahi, G.H.; et al.; A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics. Bioorg Med Chem 2002, 10, 5, 1321. |
| 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) | 30921 | 2,4(1H,3H)-pyrimidinedione; Uracil | 66-22-8 | C4H4N2O2 | 详情 | 详情 |
| (II) | 11176 | 3-Bromopropyne; 3-Bromo-1-propyne | 106-96-7 | C3H3Br | 详情 | 详情 |
| (III) | 60461 | 1-(2-propynyl)-2,4(1H,3H)-pyrimidinedione | C7H6N2O2 | 详情 | 详情 | |
| (IV) | 28793 | (Z)-1,2-dichloroethene | 156-59-2 | C2H2Cl2 | 详情 | 详情 |
| (V) | 60462 | 1-[(Z)-5-chloro-4-penten-2-ynyl]-2,4(1H,3H)-pyrimidinedione | C9H7ClN2O2 | 详情 | 详情 | |
| (VI) | 60463 | 1-[(Z)-5-chloro-4-penten-2-ynyl]-3-(2-propynyl)-2,4(1H,3H)-pyrimidinedione | C12H9ClN2O2 | 详情 | 详情 |