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【结 构 式】 
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【药物名称】MF-569, 3-IAABU 【化学名称】N-[3-(Iodoacetamido)benzoyl]urea 【CA登记号】218935-77-4 【 分 子 式 】C10H10IN3O3 【 分 子 量 】347.1139 |
【开发单位】Cytoskeleton (Originator), Mount Sinai School of Medicine (Originator), New York University (Originator) 【药理作用】ONCOLYTIC DRUGS, Antimitotic Drugs, Microtubule-Stabilizing Agents |
合成路线1
The acylation of 3-aminobenzoic acid with acetic anhydride in ethyl acetate gives the corresponding acetamide (II), which is treated with SOCl2 in refluxing ethyl acetate yielding 3-(trifluoroacetamido)benzoyl chloride (III). The reaction of (III) with urea (IV) in toluene at 100 C gives the acylated urea (V), which is deprotected with butylamine in refluxing methanol to afford N-(3-aminobenzoyl)urea (VI). The acylation of (VI) with chloroacetyl chloride (VII) in dimethylacetamide provides the corresponding amide (VIII), which is finally treated with NaI in dimethylacetamide.
| 【1】 Bekesi, J.G.; Holland, J.F.; Jiang, J.-D.; Ma, L.; Roboz, J.; Deng, L.; Weisz, I.; Synthesis, cancericidal and antimicrotubule activities of 3-(haloacetamido)-benzoylureas. Anti-Cancer Drug Des 1998, 13, 7, 735. |
| 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) | 26638 | 3-Aminobenzoic acid | 99-05-8 | C7H7NO2 | 详情 | 详情 |
| (II) | 26639 | 3-[(2,2,2-trifluoroacetyl)amino]benzoic acid | C9H6F3NO3 | 详情 | 详情 | |
| (III) | 26640 | 3-[(2,2,2-trifluoroacetyl)amino]benzoyl chloride | C9H5ClF3NO2 | 详情 | 详情 | |
| (IV) | 19310 | urea | 57-13-6 | CH4N2O | 详情 | 详情 |
| (V) | 26641 | N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide | C10H8F3N3O3 | 详情 | 详情 | |
| (VI) | 26642 | N-(3-aminobenzoyl)urea | C8H9N3O2 | 详情 | 详情 | |
| (VII) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (VIII) | 26643 | N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2-chloroacetamide | C10H10ClN3O3 | 详情 | 详情 |