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【结 构 式】 
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【药物名称】A-176120 【化学名称】5-[N-(2-Ethoxybenzyl)-N-[3-(4-methylphenoxy)benzyl]carbamoyl]-1,2,4-benzenetricarboxylic acid 【CA登记号】185049-54-1 【 分 子 式 】C33H29NO9 【 分 子 量 】583.60038 |
【开发单位】Abbott (Originator) 【药理作用】Oncolytic Drugs, Angiogenesis Inhibitors, Farnesyl Transferase Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
Reaction of 4-methylphenol (I) with NaH in DMF and 3-fluorobenzaldehyde (II) yields aldehyde (III), which will be converted into secondary amine (V) via a reductive amination with amine (IV) in presence of NaBH3CN in MeOH and catalytic HOAc. Amine (V) couples with dianhydride (VI) in THF in presence of NMM or alternatively in toluene and Et3N. Final treatment with Na2CO3 in THF yields the desired product.
| 【1】 Sullivan, G.M.; Rosenberg, S.H.; Prasad, R.N.; O'Connor, S.J.; Donner, B.G.; Fakhoury, S.A.; Fung, K.L.; Stout, D.M.; Rockway, T.W.; Baker, W.R.; Shen, W.; Garvey, D.S. (Abbott Laboratories Inc.); Benzene, pyridine, naphthalene or benzophenone derivs. as inhibitors of squalene synthetase and protein farnesyltransferase. WO 9634851 . |
| 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) | 37678 | p-cresol | 106-44-5 | C7H8O | 详情 | 详情 |
| (II) | 18887 | 3-Fluorobenzaldehyde | 456-48-4 | C7H5FO | 详情 | 详情 |
| (III) | 41482 | 3-(4-methylphenoxy)benzaldehyde | 79124-75-7 | C14H12O2 | 详情 | 详情 |
| (IV) | 38253 | 2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine | C9H13NO | 详情 | 详情 | |
| (V) | 41483 | N-(2-ethoxybenzyl)[3-(4-methylphenoxy)phenyl]methanamine; N-(2-ethoxybenzyl)-N-[3-(4-methylphenoxy)benzyl]amine | n/a | C23H25NO2 | 详情 | 详情 |
| (VI) | 41484 | 1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone | 89-32-7 | C10H2O6 | 详情 | 详情 |
Extended Information