DB-480
Chemical Name: 4,4'-(Furan-2,4-diyl)bis(N1-isopropylbenzamidine) dihydrochloride
项目整合开发状态: Preclinical
项目研究机构: University of Georgia (Originator), University of North Carolina (Originator)
合成路线:Aldol condensation of 4-cyanobenzaldehyde (II) with 4-cyano-acetophenone (I) in methanolic NaOH furnished chalcone (III).Subsequent addition of bromine to (III) gave dibromide (IV).This was treated with NaOMe to produce the intermediate enol ether (V),which was then condensed with the ylide generated from trimethylsulfonium iodide and NaH to afford the 2,4-diarylfuran (VI).Acid-catalyzed addition of EtOH to (VI) provided the corresponding bis(imidate) (VII).Further reaction of (VII) with isopropylamine yielded the target amidine,which was isolated as the dihydrochloride salt.
📌 参考资料/链接：
参考文献标题:2,4-Bis (4-amidino)phenyl furans as anti-Pneumocystis carinii agents
文献作者:Boykin,D.W.; Francesconi,I.; Tidwell,R.R.; Wilson,D.W.(Georgia State University; University of North Carolina)
参考来源:EP 0941991; GB 2334716; US 6008247
📄 详细内容
合成路线:Aldol condensation of 4-cyanobenzaldehyde (II) with 4-cyano-acetophenone (I) in methanolic NaOH furnished chalcone (III).Subsequent addition of bromine to (III) gave dibromide (IV).This was treated with NaOMe to produce the intermediate enol ether (V),which was then condensed with the ylide generated from trimethylsulfonium iodide and NaH to afford the 2,4-diarylfuran (VI).Acid-catalyzed addition of EtOH to (VI) provided the corresponding bis(imidate) (VII).Further reaction of (VII) with isopropylamine yielded the target amidine,which was isolated as the dihydrochloride salt.
参考文献标题:2,4-Diphenyl furan diamidines as novel anti-pneumocystis carinii pneumonia agents
文献作者:Francesconi,I.; Wilson,W.D.; Tanious,F.A.; Hall,J.E.; Bender,B.C.; Tidwell,R.R.; McCurdy,D.; Boykin,D.W.
参考来源:J Med Chem 1999,42(12),2260