S-DABO, HI-280
Chemical Name: 6-Benzyl-5-isopropyl-2-(methylsulfanylmethylsulfanyl)pyrimidin-4(3H)-one
CAS No. 210645-95-7
项目整合开发状态: Preclinical
项目研究机构: Parker Hughes Institute (Originator)
合成路线:The reaction of 2-phenylacetonitrile (I) with 2-bromo-3-methylbutyric acid ethyl ester (II) by means of Zn in THF gives the ketoester (III),which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding 6-benzyl-5-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V).Finally,this compound is treated with chloromethyl methyl sulfide (VI) and K2CO3 in DMF.
合成路线:The condensation of 2-(3,5-dimethylphenyl)acetonitrile (I) with ethyl 2-bromo-3-methylbutyrate (II) by means of Zn in THF gives the beta-ketoester (III),which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding the thioxopyrimidinone (V).Finally,this compound is condensed with choromethyl methyl sulfide by means of K2CO3 in DMF.
📌 参考资料/链接：
参考文献标题:Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase
文献作者:Sudbeck,E.A.; Mao,C.; Vig,R.; Venkatachalam,T.K.; Tuel-Ahlgren,L.; Uckun,F.M.
参考来源:Antimicrob Agents Chemother 1998,42(12),3225
📄 详细内容
合成路线:The reaction of 2-phenylacetonitrile (I) with 2-bromo-3-methylbutyric acid ethyl ester (II) by means of Zn in THF gives the ketoester (III),which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding 6-benzyl-5-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V).Finally,this compound is treated with chloromethyl methyl sulfide (VI) and K2CO3 in DMF.
合成路线:The condensation of 2-(3,5-dimethylphenyl)acetonitrile (I) with ethyl 2-bromo-3-methylbutyrate (II) by means of Zn in THF gives the beta-ketoester (III),which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding the thioxopyrimidinone (V).Finally,this compound is condensed with choromethyl methyl sulfide by means of K2CO3 in DMF.
参考文献标题:5-Alkyl-2-[(methylthiomethyl)thio]-6-(benzyl)-pyrimidin-4-(1H)-ones as potent non-nucleoside reverse transcriptase inhibitors of S-DABO series
文献作者:Vig,R.; Mao,C.; Venkatachalam,T.K.; Tuel-Ahlgren,L.; Sudbeck,E.A.; Uckun,F.M.
参考来源:Bioorg Med Chem Lett 1998,8(12),1461
产品链接: CAS No. 210645-95-7››