新产品编号:633309
Chemical Name: 2,5-Dihydroxy-3-(1-methylindol-3-yl)-6-phenyl-2,5-cyclohexadiene-1,4-dione
CAS No. 245737-50-2
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:Treatment of phenylacetyl chloride (I) with tris(trimethylsilyloxy)ethylene (A) in the presence of SnCl4 affords 1-hydroxy-3-phenylpropan-2-one (II),which is then condensed with ethyl oxalyl chloride (III) in THF in the presence of Et3N to yield (IV).Phenylhexanoate derivative (IV) is cyclized by means of DBU in DMF to provide valerolactone derivative (V),which is then condensed with 1-methylindole-3-carboxaldehyde (VI) in HOAc to furnish derivative (VII).Finally,the target compound is obtained by treatment of (VII) with NaOMe in MeOH.
📌 参考资料/链接：
参考文献标题:Antidiabetic agents
文献作者:Wood,H.B.; Jones,A.B.; Zhang,B.; Liu,K.(Merck & Co.,Inc.)
参考来源:EP 1067925; US 6077849; WO 9951225
📄 详细内容
合成路线:Treatment of phenylacetyl chloride (I) with tris(trimethylsilyloxy)ethylene (A) in the presence of SnCl4 affords 1-hydroxy-3-phenylpropan-2-one (II),which is then condensed with ethyl oxalyl chloride (III) in THF in the presence of Et3N to yield (IV).Phenylhexanoate derivative (IV) is cyclized by means of DBU in DMF to provide valerolactone derivative (V),which is then condensed with 1-methylindole-3-carboxaldehyde (VI) in HOAc to furnish derivative (VII).Finally,the target compound is obtained by treatment of (VII) with NaOMe in MeOH.
参考文献标题:Discovery of a potent,highly selective,and orally efficacious small-molecule activator of the insulin receptor
文献作者:Liu,K.; Xu,L.; Szalkowski,D.; Li,Z.; Ding,V.; Kwei,G.; Huskey,S.E.; Moller,D.E.; Heck,J.V.; Zhang,B.B.; Jones,A.B.
参考来源:J Med Chem 2000,43(19),3487