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【结 构 式】 
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【药物名称】AGR-129 【化学名称】N-(3-Chlorobenzyl)-2-cyano-3-[2-[3-(1H-imidazol-2-ylsulfanyl)propoxy]phenyl]-2(E)-propenamide 【CA登记号】 【 分 子 式 】C23H21ClN4O2S 【 分 子 量 】452.96642 |
【开发单位】Hebrew University (Originator) 【药理作用】ONCOLYTIC DRUGS, Farnesyl Transferase Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
Salicylaldehyde (I) was alkylated with 1,3-dibromopropane (II) to provide bromopropyl ether (III). Furter displacement of the bromine of (III) with the potassium salt of 2-mercaptoimidazole (IV) gave thioether (V). Condensation of methyl cyanoacetate (VI) with 3-chlorobenzylamine (VII) at 120 C afforded cyanoacetamide (VIII). Finally, Knoevenagel reaction of (VIII) with benzaldehyde (V) in the presence of beta-alanine furnished the title compound.
| 【1】 Gazit, A.; Levitzki, A.; Reuveni, H.; Poradosu, E.; alpha-Cyanocinnamide derivatives: A new family of non-peptide, non-sulfhydryl inhibitors of Ras farnesylation. Bioorg Med Chem 1999, 7, 8, 1727. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 17022 | beta-Alanine; 3-aminopropionic acid | 107-95-9 | C3H7NO2 | 详情 | 详情 | |
| (I) | 21351 | 2-Hydroxybenzaldehyde;Salicylic aldehyde；2-Formylphenol;salicylaldehyde | 90-02-8 | C7H6O2 | 详情 | 详情 |
| (II) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (III) | 34455 | 2-(3-bromopropoxy)benzaldehyde | C10H11BrO2 | 详情 | 详情 | |
| (IV) | 34456 | 1H-imidazole-2-thiol; 1H-imidazol-2-ylhydrosulfide | 872-35-5 | C3H4N2S | 详情 | 详情 |
| (V) | 34457 | 2-[3-(1H-imidazol-2-ylsulfanyl)propoxy]benzaldehyde | C13H14N2O2S | 详情 | 详情 | |
| (VI) | 34458 | Cyanoacetic acid methyl ester; methyl 2-cyanoacetate | 105-34-0 | C4H5NO2 | 详情 | 详情 |
| (VII) | 34459 | (3-chlorophenyl)methanamine; 3-chlorobenzylamine | 4152-90-3 | C7H8ClN | 详情 | 详情 |
| (VIII) | 34460 | N-(3-chlorobenzyl)-2-cyanoacetamide | C10H9ClN2O | 详情 | 详情 |