HI-346
Chemical Name: N-(5-Bromopyridin-2-yl)-N'-[2-(1-cyclohexenyl)ethyl]thiourea
CAS No. 167683-78-5
项目整合开发状态: Preclinical
项目研究机构: Medivir (Originator), Parker Hughes Institute (Codevelopment)
合成路线:Treatment of 2-amino-5-bromopyridine (I) with 2-(1-cyclohexenyl)ethyl isothiocyanate (II) in hot N-methylpyrrolidinone produced the target thiourea.
合成路线:Treatment of 2-amino-5-chloropyridine (I) with 2-(1-cyclohexenyl)ethyl isothiocyanate (II) in N,N-dimethylformamide at 90 C produced the target thiourea.
合成路线:2,6-Difluorophenethylamine (II) was prepared by reduction of nitrile (I) with either NaBH4 in the presence of CoCl2 or borane in THF.Reaction of amine (II) with thiocarbonyldiimidazole (III) furnished the thioimidazolide (IV).This was finally condensed with 2-amino-5-chloropyridine (V),yielding the corresponding thiourea.
📌 参考资料/链接：
参考文献标题:Cpds.and methods for inhibition of HIV and related viruses
文献作者:Lind,P.T.; Noreen,R.; Ternansky,R.J.; Morin,J.M.Jr.(Medivir AB)
参考来源:WO 9303022
📄 详细内容
合成路线: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.
合成路线:Alternatively,2-amino-5-chloropyridine (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.
参考文献标题: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
文献作者:Uckun,F.M.; Mao,C.; Pendergrass,S.; Maher,D.; Zhu,D.; Tuel-Ahlgren,L.; Venkatachalam,T.K.
参考来源:Bioorg Med Chem Lett 1999,9(18),2721