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【结 构 式】 
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【药物名称】 【化学名称】3'-Azido-5'-O-[4-bromophenoxy[1-(methoxycarbonyl)ethylamino]phosphoryl]-3'-deoxythymidine 【CA登记号】220693-38-9 【 分 子 式 】C20H24BrN6O8P 【 分 子 量 】587.32748 |
【开发单位】Parker Hughes Institute (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, Reverse Transcriptase Inhibitors |
合成路线1
Treatment of p-bromophenol (I) with phosphoryl chloride and triethylamine furnished p-bromophenyl phosphorodichloridate (II), which was condensed with alanine methyl ester (III) to give the intermediate phosphorochloridate (IV). Then, coupling of chloridate (IV) with azidothimidine (V) in the presence of N-methylimidazole yielded the title compound.
| 【1】 Venkatachalam, T.K.; Zhu, Z.; Shih, M.-J.; Tai, H.-L.; Uckun, F.M.; Jan, S.-T.; AZT-5'-(p-bromophenyl methoxyalaninyl phosphate) as a potent and non-toxic anti-human immunodeficiency virus agent. Antivir Chem Chemother 1999, 10, 1, 47. |
| 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) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (II) | 25314 | Dichlorophoephoric acid 4-bromophenyl ester | C6H4BrCl2O2P | 详情 | 详情 | |
| (III) | 25315 | methyl 2-aminopropanoate; Alanine, methyl ester | 7625-53-8 | C4H9NO2 | 详情 | 详情 |
| (IV) | 25316 | methyl 2-[[(4-bromophenoxy)(chloro)phosphoryl]amino]propanoate | C10H12BrClNO4P | 详情 | 详情 | |
| (V) | 25317 | 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione | 101703-35-9 | C10H13N5O4 | 详情 | 详情 |
Extended Information