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新产品编号:2425715

Chemical Name: 4,6-Dichloro-3-(2,4-dioxo-3-phenylimidazolidin-1-ylmethyl)-1H-indole-2-carboxylic acid
项目整合开发状态: Preclinical
项目研究机构: Johannes Gutenberg-Universit鋞 Mainz (Originator)
合成路线:Diazotization of 3,5-dichloroaniline (I),followed by reduction of the resultant diazonium salt provides hydrazine (II).Subsequent reaction of 3,5-dichlorophenylhydrazine (II) with ethyl pyruvate (III) under Fischer reaction conditions gives rise to indole (IV).Vilsmeier formylation of (IV) using N-methylformanilide and phosphoryl chloride produces aldehyde (V).This is reductively aminated with methyl glycinate and NaBH(OAc)3 to afford aminoester (VI).Condensation of (VI) with phenyl isocyanate,followed by cyclization in the presence of Et3N leads to hydantoin (VII).Finally,ester (VII) is hydrolyzed employing LiOH to furnish the target indolecarboxylic acid.
📌 参考资料/链接:
参考文献标题:Hydantoin-substituted 4,6-dichloroindole-2-carboxylic acids as ligands with high affinity for the glycine binding site of the NMDA receptor
文献作者:Jansen,M.; Potschka,H.; Brandt,C.; Lcher,W.; Dannhardt,G.
参考来源:J Med Chem 2003,46(1),64