ZK-805412(free base)
Chemical Name: (Z,Z)-2,7-Bis(4-amidinobenzylidene)cycloheptanone trifluoroacetate
项目整合开发状态: Biological Testing
项目研究机构: Berlex (Originator)
合成路线:Aldol condensation of cycloheptanone (I) with two molecules of 4-amidinobenzaldehyde.HCl (II) in 85% phosphoric acid at 100 C provided the E,E-bis(benzylidene) compound (III).Photoisomerization of (III) in a H2O-acetonitrile solution produced an equilibrium mixture of a 55% of E,Z isomer (IV),a 40% of Z,Z isomer (V),and < 5% of the starting E,E isomer (III),which were separated by reverse-phase HPLC.
📌 参考资料/链接：
参考文献标题:(Z,Z)-2,7-Bis(4-amidinobenzylidene)cycloheptan-1-one: Identification of a highly active inhibitor of blood coagulation factor Xa
文献作者:Shaw,K.J.; Guilford,W.J.; Dallas,J.L.; Koovakkaat,S.K.; McCarrick,M.A.; Liang,A.; Light,D.R.; Morrissey,M.M.
参考来源:J Med Chem 1998,41(19),3551-3556
📄 详细内容
合成路线:The condensation of cycloheptanone (I) with 4-iodobenzaldehyde (II) gives the (E,E)-bis-benzylidene derivative (III),which by irradiation with UV light is converted into the (Z,Z)-isomer (IV).The reaction of (IV) with CuCN in DMF affords the mono-cyano derivative (V),which is then treated with Cu-11CN in DMF to provide the labeled dicyano derivative (VI).Finally,this compound is treated with ammonia in methanol to afford the target labeled bis-amidino derivative.
参考文献标题:Total synthesis and radiolabelling of an efficient rt-PA inhibitor: [11C] (Z,Z)-BABCH.A first route to [11C] labelled amidines
文献作者:Simeon,F.; et al.
参考来源:J Chem Soc - Perkins Trans I 2001,(7),690