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【结 构 式】 
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【药物名称】FTI-2148 【化学名称】N-[5-(1H-Imidazol-4-ylmethylaminomethyl)-2'-methylbiphenyl-2-ylcarbonyl]-L-methionine 【CA登记号】251577-09-0 【 分 子 式 】C24H28N4O3S 【 分 子 量 】452.57976 |
【开发单位】H. Lee Moffitt Center (Originator), London School Hygiene Tropical Medicine (Originator), Seattle Biomedical Research Institute (Originator), University of Washington (Originator), Yale University (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Oncolytic Drugs, Treatment of Protozoal Diseases, Farnesyl Transferase Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
Reductive amination of the methionine methyl ester adduct of 2-(2-methylphenyl)-4-aminomethyl benzoic acid (I) with 1-trityl-4-formylimidazole (II) gave the secondary amine (III). After trityl group deprotection, the resultant methyl ester (IV) was hydrolyzed to the target carboxylic acid by using LiOH.
| 【1】 Blaskovich, M.A.; Hamilton, A.D.; Sun, J.; Knowles, D.; Bailey, R.D.; Sebti, S.M.; Ohkanda, J.; Qian, Y.; Antitumor efficacy of a novel class of non-thiol-containing peptidomimetic inhibitors of farnesyltransferase and geranylgeranyltransferase I: Combination therapy with the cytotoxic agents cisplatin, Taxol, and gemcitabine. Cancer Res 1999, 59, 19, 4919. |
| 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) | 50133 | methyl (2S)-2-([[5-(aminomethyl)-2'-methyl[1,1'-biphenyl]-2-yl]carbonyl]amino)-4-(methylsulfanyl)butanoate | C21H26N2O3S | 详情 | 详情 | |
| (II) | 27712 | 1-trityl-1H-imidazole-4-carbaldehyde；1-Tritylimidazole-4-carboxaldehyde | 33016-47-6 | C23H18N2O | 详情 | 详情 |
| (III) | 50134 | methyl (2S)-4-(methylsulfanyl)-2-([[2'-methyl-5-([[(1-trityl-1H-imidazol-4-yl)methyl]amino]methyl)[1,1'-biphenyl]-2-yl]carbonyl]amino)butanoate | C44H44N4O3S | 详情 | 详情 | |
| (IV) | 50135 | methyl (2S)-2-[[(5-[[(1H-imidazol-4-ylmethyl)amino]methyl]-2'-methyl[1,1'-biphenyl]-2-yl)carbonyl]amino]-4-(methylsulfanyl)butanoate | C25H30N4O3S | 详情 | 详情 |