BRACO-19
Chemical Name: N,N'-[9-[4-(Dimethylamino)phenylamino]acridin-3,6-diyl]bis[3-(1-pyrrolidinyl)propionamide] trihydrochloride
CAS No. 351351-75-2
项目整合开发状态: Preclinical
项目研究机构: Cancer Research Technology (Originator)
合成路线:Diphenylmethane (I) is nitrated to the tetranitro derivative (II) employing KNO3 in concentrated H2SO4.Oxidation of the diarylmethane (II) with CrO3 in boiling HOAc provides benzophenone (III).Cyclization of (III) under reductive conditions gives rise to the diamino acridone (IV),which is further acylated by 3-chloropropionyl chloride (V) to the bis-chloropropionamide (VI).Nucleophilic substitution of the chloride groups of (VI) with pyrrolidine (VII) furnishes the bis-pyrrolidino derivative (VIII).Chlorination of acridone (VIII) with POCl3 yields the chloroacridine (IX).This is finally condensed with 4-(dimethylamino)aniline (X) to produce the title compound.
📌 参考资料/链接：
参考文献标题:Therapeutic acridone and acridine cpds.
文献作者:Neidle,S.; Harrison,R.J.; Kelland,L.R.; Gowan,S.M.; Read,M.; Reszka,T.(Cancer Research Technology Ltd.)
参考来源:WO 0208193
📄 详细内容
合成路线:Diphenylmethane (I) is nitrated to the tetranitro derivative (II) employing KNO3 in concentrated H2SO4.Oxidation of the diarylmethane (II) with CrO3 in boiling HOAc provides benzophenone (III).Cyclization of (III) under reductive conditions gives rise to the diamino acridone (IV),which is further acylated by 3-chloropropionyl chloride (V) to the bis-chloropropionamide (VI).Nucleophilic substitution of the chloride groups of (VI) with pyrrolidine (VII) furnishes the bis-pyrrolidino derivative (VIII).Chlorination of acridone (VIII) with POCl3 yields the chloroacridine (IX).This is finally condensed with 4-(dimethylamino)aniline (X) to produce the title compound.
参考文献标题:Structure-based design of selective and potent G quadruplex-mediated telomerase inhibitors
文献作者:Read,M.; Harrison,R.J.; Romagnoli,B.; Tanious,F.A.; Gowan,S.H.; Reszka,A.P.; Wilson,W.D.; Kelland,L.R.; Neidle,S.
参考来源:Proc Natl Acad Sci USA 2001,98(9),4844
产品链接: CAS No. 351351-75-2››