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【结 构 式】 
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【药物名称】YW-355 【化学名称】(±)-N-[2-[1-(Chloromethyl)-5-hydroxy-2,3-dihydro-1H-benzo[e]indol-3-ylcarbonyl]-1H-indol-5-yl]-5-nitro-1-benzofuran-2-carboxamide 【CA登记号】500536-50-5 【 分 子 式 】C31H21ClN4O6 【 分 子 量 】580.98922 |
【开发单位】Panorama Research (Originator) 【药理作用】Oncolytic Drugs, Apoptosis Inducers |
合成路线1
Coupling between ethyl 5-aminoindole-2-carboxylate (I) and 5-nitrobenzofuran-2-carboxylic acid (II) by means of HBTU affords amide (III). Subsequent ethyl ester hydrolysis under alkaline conditions yields the carboxylic acid (IV). Ring opening of the cyclopropane-fused compound (V) with anhydrous HCl in EtOAc leads to the chloromethyl compound (VI). Acid (IV) is finally coupled to amine (VI) in the presence of EDC to furnish the title compound.
| 【1】 Wang, Y.; Li, L.; Ye, W.; Tian, Z.; Jiang, W.; Wang, H.; Wright, S.C.; Larrick, J.W.; CC-1065 analogues bearing different DNA-binding subunits: Synthesis, antitumor activity, and preliminary toxicity study. J Med Chem 2003, 46, 4, 634. |
| 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) | 38164 | ethyl 5-amino-1H-indole-2-carboxylate | C11H12N2O2 | 详情 | 详情 | |
| (II) | 63365 | 5-nitro-1-benzofuran-2-carboxylic acid | 10242-12-3 | C9H5NO5 | 详情 | 详情 |
| (III) | 63366 | ethyl 5-{[(5-nitro-1-benzofuran-2-yl)carbonyl]amino}-1H-indole-2-carboxylate | C20H15N3O6 | 详情 | 详情 | |
| (IV) | 63367 | 5-{[(5-nitro-1-benzofuran-2-yl)carbonyl]amino}-1H-indole-2-carboxylic acid | C18H11N3O6 | 详情 | 详情 | |
| (V) | 40978 | 1,2,2a,3,9,9a-hexahydro-4H-benzo[e]cyclopropa[c]indol-4-one | C13H13NO | 详情 | 详情 | |
| (VI) | 40977 | 1-(chloromethyl)-2,3-dihydro-1H-benzo[e]indol-5-ol | C13H12ClNO | 详情 | 详情 |
Extended Information