Zalospirone hydrochloride, Wy-47846
扎螺酮 Chemical Name: 3a,4,4a,6a,7,7a-Hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-4,7-etheno-1H-cyclobut[f]isoindole-1,3(2H)-dione hydrochloride; endo-(3aalpha,4alpha,4abeta,6abeta,7alpha,7aalpha)-Hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-4,7-etheno-1H-cyclobut[f]isoindole-1,3(2H)-dione hydrochloride; (1R*,2R*,5S*,6S*,7S*,8R*)-N-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]tricyclo[4.2.2.0(2,5)]deca-3,9-diene-7,8-dicarboximide hydrochloride
CAS No. 110944-55-3, 114298-18-9 (free base, no stereoch.), 114374-97-9 (undefined stereoch.)
项目整合开发状态: Phase II
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:Reaction of 1,3,5,7-cyclooctatetraene (I) with maleimide (Step a,b),or maleic anhydride (Step c),in refluxing toluene affords the imide (II) or the anhydride (III) in 78 and 85% yields,respectively.Reaction of imide intermediate (II) with 1,4-dibromobutane gives the omega-haloalkylimide,which subsequently is reacted with 1-(2-pyrimidinyl)piperazine to yield Wy-47846 (Method A).Alternatively,Wy-47846 can be prepared via the reaction of (III) with 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine in refluxing pyridine (Method B),as shown in scheme.Wy-47846 is achiral.
📌 参考资料/链接：
参考文献标题:Polycyclic aryl- and heteroarylpiperazyl imides as 5-HT1A receptor ligands and potential anxiolytic agents: synthesis and structure-activity relationship studies
文献作者:Abou-Gharbia,M.; et al.
参考来源:J Med Chem 1988,31(7),1382
📄 详细内容
合成路线:Reaction of 1,3,5,7-cyclooctatetraene (I) with maleimide (Step a,b),or maleic anhydride (Step c),in refluxing toluene affords the imide (II) or the anhydride (III) in 78 and 85% yields,respectively.Reaction of imide intermediate (II) with 1,4-dibromobutane gives the omega-haloalkylimide,which subsequently is reacted with 1-(2-pyrimidinyl)piperazine to yield Wy-47846 (Method A).Alternatively,Wy-47846 can be prepared via the reaction of (III) with 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine in refluxing pyridine (Method B),as shown in scheme.Wy-47846 is achiral.
参考文献标题:WY-47846
文献作者:Abou-Gharbia,M.; Moyer,J.A.; Haskins,J.T.
参考来源:Drugs Fut 1989,14(5),442
产品链接: CAS No.114298-18-9››