VN-2142
Chemical Name: 1-(2-Methoxyphenyl)-4-[3-(1-naphthyloxy)-3-(3-thienyl)propyl]piperazine hydrochloride
项目整合开发状态: Preclinical
项目研究机构: Universidad de Navarra (Originator), Vita (Originator)
合成路线:Mannich reaction of N-(2-methoxyphenyl)piperazine (I) with 3-acetylbenzothiophene (II) in the presence of paraformaldehyde and HCl in refluxing EtOH leads to the piperazinyl propanone (III).Subsequent keto group reduction with NaBH4 gives the target alcohol.
合成路线:Mannich reaction of N-(2-methoxyphenyl)piperazine (I) with 3-acetylthiophene (II) in the presence of paraformaldehyde and HCl in refluxing EtOH leads to the piperazinyl propanone (III).Subsequent keto group reduction with NaBH4 gives alcohol (IV).This is then condensed with 1-fluoronaphthalene (V) in the presence of NaH to produce the title naphthyl ether.
📌 参考资料/链接：
参考文献标题:Cpds.derived from thiophene and benzothiophene,and related utilisation and compsn.
文献作者:Bosch Rovira,A.; Roca Acin,J.; Monge Vega,A.; Del Rio Zambrana,J.; Palop Cubillo,J.A.; Lasheras Aldaz,B.; Del Castillo Nieto,J.C.(Laboratorios Vita,SA)
参考来源:EP 1008594; ES 2128266; JP 2002511883; US 6262056; WO 9902516
📄 详细内容
合成路线:Mannich reaction of N-(2-methoxyphenyl)piperazine (I) with 3-acetylbenzothiophene (II) in the presence of paraformaldehyde and HCl in refluxing EtOH leads to the piperazinyl propanone (III).Subsequent keto group reduction with NaBH4 gives the target alcohol.
合成路线:Mannich reaction of N-(2-methoxyphenyl)piperazine (I) with 3-acetylthiophene (II) in the presence of paraformaldehyde and HCl in refluxing EtOH leads to the piperazinyl propanone (III).Subsequent keto group reduction with NaBH4 gives alcohol (IV).This is then condensed with 1-fluoronaphthalene (V) in the presence of NaH to produce the title naphthyl ether.
参考文献标题:New 1-aryl-3-(4-arylpiperazin-1-yl)propane derivatives,with dual action at 5-HT1A serotonin receptors and serotonin transporter,as a new class of antidepressants
文献作者:Mart韓ez-Esparza,J.; Oficialdegui,A.-M.; P閞ez-Sailanes,S.; Heras,B.; Orus,L.; Palop,J.A.; Lasheras,B.; Roca,J.; Mourelle,M.; Bosch,A.; Del Castillo,J.C.; Tordera,R.; del Rio,J.; Monge,A.
参考来源:J Med Chem 2001,44(3),418