EF-7412
Chemical Name: N-[3-[4-[4-(1,3-Dioxoperhydro-1H-pyrrolo[1,2-c]imidazol-2-yl)butyl]piperazin-1-yl]phenyl]ethanesulfonamide
项目整合开发状态: Preclinical
项目研究机构: Universidad Complutense de Madrid (Originator)
合成路线:Perhydropyrrolo[1,2-c]imidazole-1,3-dione (II) was prepared by Urech synthesis upon condensation of proline (I) with potassium cyanate,followed by acid cyclization.Subsequent alkylation of (II) with 1-bromo-4-chlorobutane (III) in the presence of NaH in DMF provided the chlorobutyl derivative (IV).This was finally coupled with aryl piperazine (V) to yield the title compound.
📌 参考资料/链接：
参考文献标题:New arylpiperazine derivs.
文献作者:Lopez Rodriguez,M.L.; Rosado Samitier,M.L.; Benahmu Salama,B.; Fernandez Velando,E.; Morcillo Ortega,M.J.(Universidad Complutense de Madrid)
参考来源:ES 2095811; WO 9606846
📄 详细内容
合成路线:The condensation of perhydropyrrolo[1,2-c]imidazole-2,7-dione (I) with 1,4-dibromobutane (II) by means of NaH in DMF gives the expected 4-bromobutyl derivative (III),which is condensed with 1-(3-nitrophenyl)piperazine (IV) by means of triethylamine in hot acetonitrile yielding 2-[4-[4-(3-nitrophenyl)piperazin-1-yl]butyl]perhydropyrrolo[1,2-c]imidazole-2,7-dione (V).The reduction of the nitro group of (V) with H2 over Pd/C in methanol affords the corresponding amino derivative (VI),which is finally sulfonated with ethanesulfonyl chloride and pyridine in acetone.
参考文献标题:Design and synthesis of 2-[4-[4-(m-(ethylsulfonamido)-penhyl)piperazin-1-yl]butyl]-1,3-dioxoperhydropyrrolo[1,2-c]imidazole (EF-7412) using neural networks.A selective derivative with mixed 5-HT1A/D2 antagonist properties
文献作者:L髉ez-Rodr韌uez,M.L.; Morcillo,M.J..; Fernandez,E.; Rosado,M.L.; Orensanz,L.; Beneytez,M.E.; Manzanares,J.; Fuentes,J.A.; Schaper,K.J.
参考来源:Bioorg Med Chem Lett 1999,9(12),1679