CX-659S
Chemical Name: N-(6-Amino-3-methyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2(S)-carboxamide
项目整合开发状态: Preclinical
项目研究机构: Japan Energy (Originator)
合成路线:Acylation of urea derivative (I) with cyanoacetic acid (II) in HOAc in the presence of Ac2O yields derivative (III),which is then cyclized by treatment with NaOH to provide (IV).Nitrosation of (IV) with NaNO2 and HCl affords nitroso derivative (V),which is then hydrogenated over Pd/C in EtOH to furnish substituted pyrimidinedione (VI).Finally,(VI) is coupled to Trolox (VII) with N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDC稨Cl) and 1-hydroxybenzotriazole (HOBt) in DMF or with 4-(dimethylamino)pyridine (DMAP) and N-dicyclohexylcarbodiimide (DCC) in CH2Cl2 to yield the target compound.
📌 参考资料/链接：
参考文献标题:Hydroquinone derivs.and their medicinal use
文献作者:Isobe,Y.; Goto,Y.; Tobe,M.; Takahashi,O.(Japan Energy Corp.)
参考来源:JP 1998147575; US 5821247
📄 详细内容
合成路线:Acylation of urea derivative (I) with cyanoacetic acid (II) in HOAc in the presence of Ac2O yields derivative (III),which is then cyclized by treatment with NaOH to provide (IV).Nitrosation of (IV) with NaNO2 and HCl affords nitroso derivative (V),which is then hydrogenated over Pd/C in EtOH to furnish substituted pyrimidinedione (VI).Finally,(VI) is coupled to Trolox (VII) with N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDC稨Cl) and 1-hydroxybenzotriazole (HOBt) in DMF or with 4-(dimethylamino)pyridine (DMAP) and N-dicyclohexylcarbodiimide (DCC) in CH2Cl2 to yield the target compound.
参考文献标题:Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
文献作者:Tobe,M.; Isobe,Y.; Goto,Y.; Obara,F.; Tsuchiya,M.; Matsui,J.; Hirota,K.; Hayashi,H.
参考来源:Bioorg Med Chem 2000,8(8),2037