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【结 构 式】 
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【药物名称】3-BAABU, MF-191 【化学名称】N-[3-(Bromoacetamido)benzoyl]urea 【CA登记号】209345-04-0 【 分 子 式 】C10H10BrN3O3 【 分 子 量 】300.1135 |
【开发单位】Cytoskeleton (Originator), Mount Sinai School of Medicine (Originator) 【药理作用】ONCOLYTIC DRUGS, Antimitotic Drugs, Microtubule-Stabilizing Agents |
合成路线1
3-Aminobenzoic acid (I) was protected as the trifluoroacetamide (II) using trifluoroacetic anhydride and then converted to acid chloride (III) by means of SOCl2. Subsequent condensation of (III) with urea provided 3-(trifluoroacetamido)benzoylurea (IV). After cleavage of the trifluoroacetamido group of (IV) by treatment with methanolic n-butylamine, the deprotected aniline (V) was coupled with bromoacetyl bromide in DMA to furnish the title bromoacetamide.
| 【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 |
|---|---|---|---|---|---|---|
| 14005 | 2-Bromoacetyl bromide; Bromoacetyl bromide | 598-21-0 | C2H2Br2O | 详情 | 详情 | |
| 19310 | urea | 57-13-6 | CH4N2O | 详情 | 详情 | |
| (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) | 26641 | N-(3-[[(aminocarbonyl)amino]carbonyl]phenyl)-2,2,2-trifluoroacetamide | C10H8F3N3O3 | 详情 | 详情 | |
| (V) | 26642 | N-(3-aminobenzoyl)urea | C8H9N3O2 | 详情 | 详情 |