NE-2001
Chemical Name: 4'-[4-(Guanidinomethyl)benzoyloxy]biphenyl-4-carboxylic acid 4-methylbenzyl ester hydrochloride
CAS No. 508195-41-3
项目整合开发状态: Biological Testing
项目研究机构: Nanjing University (Originator), Shanghai East Best Biopharm. Enterprises (Codevelopment)
合成路线:O-Methyl isourea disulfate (I) is condensed with 4-aminomethylbenzoic acid (II) in 2 N NaOH solution to produce the corresponding guanidine,which is isolated as the hydrochloride salt (III).(1,2)
合成路线:Esterification of 4'-hydroxybiphenyl-4-carboxylic acid (IV) with MeOH in the presence of H2SO4 produces the methyl ester (V),which is further transesterified with 4-methylbenzyl alcohol (VI) under basic conditions to generate the corresponding methylbenzyl ester (VII).Phenol (VII) is finally coupled with 4-(guanidinomethyl)benzoic acid (III) by means of DCC/pyridine to yield the target guanidino diester.(1,2)
📌 参考资料/链接：
参考文献标题:Methods and compsns.for treating or preventing bacterial infection
文献作者:Muramatsu,M.; Xie,J.; Zhu,D.; Wang,M.; Cheng,N.(Nanjing University; Shanghai East Best Biopharmaceutical Enterprises Co.,Ltd.)
参考来源:US 2003125384; US 6734212; WO 0329201
📄 详细内容
合成路线:O-Methyl isourea disulfate (I) is condensed with 4-aminomethylbenzoic acid (II) in 2 N NaOH solution to produce the corresponding guanidine,which is isolated as the hydrochloride salt (III).(1,2)
合成路线:Esterification of 4'-hydroxybiphenyl-4-carboxylic acid (IV) with MeOH in the presence of H2SO4 produces the methyl ester (V),which is further transesterified with 4-methylbenzyl alcohol (VI) under basic conditions to generate the corresponding methylbenzyl ester (VII).Phenol (VII) is finally coupled with 4-(guanidinomethyl)benzoic acid (III) by means of DCC/pyridine to yield the target guanidino diester.(1,2)
参考文献标题:A specific anti-Helicobacter pylori agent NE2001: Synthesis and its effect on the growth of H.pylori
文献作者:Cheng,N.; Xie,J.-S.; Zhang,M.-Y.; Shu,C.; Zhu,D.-X.
参考来源:Bioorg Med Chem Lett 2003,13(16),2703