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【结 构 式】 
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【药物名称】BU-99006 【化学名称】2-(5-Isothiocyanato-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
【CA登记号】 【 分 子 式 】C12H9N3OS 【 分 子 量 】243.28903 |
【开发单位】University of Bristol (Originator) 【药理作用】Pharmacological Tools |
合成路线1
5-Nitrosalicylaldehyde (I) was condensed with diethyl bromomalonate (II) to give ethyl 5-nitrobenzofuran-2-carboxylate (III), which was converted into the corresponding primary amide (IV) by reaction with ethanolic ammonia. Dehydration of amide (IV) to the nitrile (V) was effected by treatment with POCl3. After formation of imidate (VI) with HCl/MeOH, cyclization with ethylenediamine produced the imidazoline (VII). The nitro group of (VII) was then reduced to amine (VIII) using Fe and HCl. This was finally converted to the title isothiocyanate by reaction with thiophosgene.
| 【1】 Hudson, A.L.; Nutt, D.J.; Grundt, P.; Coates, P.A.; Husbands, S.M.; Tyacke, R.; Robinson, E.S.J.; Lewis, J.W.; Probes for imidazole binding sites: Synthesis and evaluation of a selective, irreversible I2 ligand. Bioorg Med Chem Lett 2000, 10, 6, 605. |
| 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) | 42307 | 2-hydroxy-5-nitrobenzaldehyde；5-nitrosalicylaldehyde | 97-51-8 | C7H5NO4 | 详情 | 详情 |
| (II) | 35647 | diethyl 2-bromomalonate | 685-87-0 | C7H11BrO4 | 详情 | 详情 |
| (III) | 42308 | ethyl 5-nitro-1-benzofuran-2-carboxylate | 69404-00-8 | C11H9NO5 | 详情 | 详情 |
| (IV) | 42309 | 5-nitro-1-benzofuran-2-carboxamide | C9H6N2O4 | 详情 | 详情 | |
| (V) | 42310 | 5-nitro-1-benzofuran-2-carbonitrile | C9H4N2O3 | 详情 | 详情 | |
| (VI) | 42311 | methyl 5-nitro-1-benzofuran-2-carboximidoate | C10H8N2O4 | 详情 | 详情 | |
| (VII) | 42312 | 2-(5-nitro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole | C11H9N3O3 | 详情 | 详情 | |
| (VIII) | 42313 | 2-(4,5-dihydro-1H-imidazol-2-yl)-1-benzofuran-5-amine; 2-(4,5-dihydro-1H-imidazol-2-yl)-1-benzofuran-5-ylamine | C11H11N3O | 详情 | 详情 |