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【结 构 式】 
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【药物名称】HI-346 【化学名称】N-(5-Bromopyridin-2-yl)-N'-[2-(1-cyclohexenyl)ethyl]thiourea 【CA登记号】167683-78-5 【 分 子 式 】C14H18BrN3S 【 分 子 量 】340.28766 |
【开发单位】Medivir (Originator), Parker Hughes Institute (Codevelopment) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Reverse Transcriptase Inhibitors |
合成路线1
Treatment of 2-amino-5-bromopyridine (I) with 2-(1-cyclohexenyl)ethyl isothiocyanate (II) in hot N-methylpyrrolidinone produced the target thiourea.
| 【1】 Lind, P.T.; Noreen, R.; Ternansky, R.J.; Morin, J.M. Jr. (Medivir AB); Cpds. and methods for inhibition of HIV and related viruses. WO 9303022 . |
合成路线2
Alternatively, 2-amino-5-bromopyridine (I) was reacted with 1,1'-thiocarbonyldiimidazole (III) in acetonitrile yielding thioimidazolide (IV), which was then condensed with 2-(1-cyclohexenyl)ethylamine (V) in hot DMF.
| 【1】 Maher, D.; Mao, C.; Pendergrass, S.; Venkatachalam, T.K.; Zhu, D.; Tuel-Ahlgren, L.; Uckun, F.M.; N-[2-(1-Cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1. Bioorg Med Chem Lett 1999, 9, 18, 2721. |
| 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) | 12123 | 5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine | 1072-97-5 | C5H5BrN2 | 详情 | 详情 |
| (III) | 11990 | Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole | 6160-65-2 | C7H6N4S | 详情 | 详情 |
| (IV) | 24645 | N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide | C9H7BrN4S | 详情 | 详情 | |
| (V) | 36902 | 2-(1-cyclohexen-1-yl)ethylamine; 2-(1-cyclohexen-1-yl)-1-ethanamine; 2-(1-Cyclohexenyl)ethylamine | 3399-73-3 | C8H15N | 详情 | 详情 |
Extended Information