新产品编号:1682175
Chemical Name: 4,4'-(Furan-2,5-diyl)bis[N-(4-fluorophenoxycarbonyl)benzamidine]
项目整合开发状态: Preclinical
项目研究机构: Georgia State University (Originator), University of North Carolina (Originator)
合成路线:2,5-Bis(p-bromophenyl)furan (II) was prepared by cyclodehydration of diketone (I) in refluxing acetic anhydride.Displacement of both bromine atoms by copper(I) cyanide in boiling quinoline generated the dicyano derivative (V).Alternatively,furan (V) was prepared by addition of p-cyanobenzaldehyde (III) to divinyl sulfone (IV) in the presence of a thiazolium catalyst.After conversion of the cyano groups of (V) into bis-imidate (VI),reaccion with ethanolic ammonia furnished amidine (VII).The stable symmetrical carbonate (X) was obtained by reaction of p-fluorophenyl chloroformate (VIII) with p-fluorophenol (IX) in the presence of pyridine.Finally,reaction of the bis(amidine) compound (VII) with carbonate (X) yielded the title compound.
📌 参考资料/链接：
参考文献标题:Prodrugs for amidines: Synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan
文献作者:Rahmathullah,S.M.; Hall,J.E.; Bender,B.C.; McCurdy,D.R.; Tidwell,R.R.; Boykin,D.W.
参考来源:J Med Chem 1999,42(19),3994
📄 详细内容
合成路线:The Friedel Crafts condensation of fumaryl chloride (I) with bromobenzene (II) gives 1,2-bis(4-bromobenzoyl)ethylene (III),which is reduced with Zn and Ac-OH to yield 1,4-bis(4-bromophenyl)butane-1,4-dione (IV).The cyclization of (IV) in refluxing Ac2O affords 2,5-bis(4-bromophenyl)furan (V) which is treated with CNCu in refluxing quinoline to provide 2,5-bis(4-cyanophenyl)furan (VI).The reaction of (VI) with HCl in ethanol gives the bis imidate (VII),which is finally treated with ammonia in ethanol to yield the target bis benzamidine.
合成路线:2,5-Bis(p-bromophenyl)furan (II) was prepared by cyclodehydration of diketone (I) in refluxing acetic anhydride.Displacement of both bromine atoms by copper(I) cyanide in boiling quinoline generated the dicyano derivative (V).Alternatively,furan (V) was prepared by addition of p-cyanobenzaldehyde (III) to divinyl sulfone (IV) in the presence of a thiazolium catalyst.After conversion of the cyano groups of (V) into bis-imidate (VI),reaccion with ethanolic ammonia furnished amidine (VII).The stable symmetrical carbonate (X) was obtained by reaction of p-fluorophenyl chloroformate (VIII) with p-fluorophenol (IX) in the presence of pyridine.Finally,reaction of the bis(amidine) compound (VII) with carbonate (X) yielded the title compound.
参考文献标题:Synthesis and antiprotozoal activity of 2,5-bis (4-guanylphenyl) furans
文献作者:Das,B.P.; Boykin,D.W.
参考来源:J Med Chem 1977,20(4),531-536
合成路线:2,5-Bis(p-bromophenyl)furan (II) was prepared by cyclodehydration of diketone (I) in refluxing acetic anhydride.Displacement of both bromine atoms by copper(I) cyanide in boiling quinoline generated the dicyano derivative (V).Alternatively,furan (V) was prepared by addition of p-cyanobenzaldehyde (III) to divinyl sulfone (IV) in the presence of a thiazolium catalyst.After conversion of the cyano groups of (V) into bis-imidate (VI),reaccion with ethanolic ammonia furnished amidine (VII).The stable symmetrical carbonate (X) was obtained by reaction of p-fluorophenyl chloroformate (VIII) with p-fluorophenol (IX) in the presence of pyridine.Finally,reaction of the bis(amidine) compound (VII) with carbonate (X) yielded the title compound.
参考文献标题:
文献作者:Kawada,A.; Aragane,Y.; Maeda,A.; Tezuka,T.
参考来源:Heterocycl Commun 1996,2(2),135-140