BMS-247615, TAS-103
TAS-103二盐酸盐 6-[[2-(二甲基氨基)乙基]氨基]-3-羟基-7H-茚并[2,1-C]喹啉-7-酮 Chemical Name: 6-[2-(Dimethylamino)ethylamino]-3-hydroxy-7H-indeno[2,1-c]quinolin-7-one dihydrochloride
CAS No. 174634-09-4, 174634-08-3 (free base)
项目整合开发状态: Phase II
项目研究机构: Taiho (Originator), Bristol-Myers Squibb (Licensee)
合成路线:Racemic lometrexol has been prepared.
合成路线:The condensation of 1,3-dioxoindane-2-carboxylic acid ethyl ester (I) with m-anisidine (II) in refluxing toluene gives the corresponding amide (III),which is cyclized with polyphosphoric acid (PPA) at 120 C yielding 3-methoxy-6,7-dihydro-5H-indeno[2,1-c]quinoline-6,7-dione (IV).The reaction of (IV) with refluxing POCl3 affords the chloroketone (V),which is condensed with 2-(dimethylamino)ethylamine (VI) in pyridine at 100 C giving the aminoketone (VII).Finally,this compound is demethylated with concentrated HBr in refluxing acetic acid.
📌 参考资料/链接：
参考文献标题:Novel fused indan deriv.and pharmaceutically acceptable salt
文献作者:Okazaki,S.; Asao,T.; Wakida,M.; Ishida,K.; Washinosu,M.; Utsugi,T.; Yamada,Y.(Taiho Pharmaceutical Co.,Ltd.)
参考来源:EP 0713870; US 5710162; US 5733918; WO 9532187
📄 详细内容
合成路线:The condensation of 1,3-dioxoindane-2-carboxylic acid ethyl ester (I) with m-anisidine (II) in refluxing toluene gives the corresponding amide (III),which is cyclized with polyphosphoric acid (PPA) at 120 C yielding 3-methoxy-6,7-dihydro-5H-indeno[2,1-c]quinoline-6,7-dione (IV).The reaction of (IV) with refluxing POCl3 affords the chloroketone (V),which is condensed with 2-(dimethylamino)ethylamine (VI) in pyridine at 100 C giving the aminoketone (VII).Finally,this compound is demethylated with concentrated HBr in refluxing acetic acid.
参考文献标题:Synthesis of novel indeno[2,1-c]quinolin-7-one derivatives and their topoisomerase inhibitory and antitumor activities
文献作者:Ishida,K.; Wakida,M.; Utsugi,T.; Okazaki,S.; Yamada,Y.; Asano,T.
参考来源:17th Symp Med Chem/6th Annu Meet Div Med Chem/2nd Conf Drug Discov (Nov 19-21,Tsukuba) 1997,Abst 2-P-05.
合成路线:The condensation of 1,3-dioxoindane-2-carboxylic acid ethyl ester (I) with m-anisidine (II) in refluxing toluene gives the corresponding amide (III),which is cyclized with polyphosphoric acid (PPA) at 120 C yielding 3-methoxy-6,7-dihydro-5H-indeno[2,1-c]quinoline-6,7-dione (IV).The reaction of (IV) with refluxing POCl3 affords the chloroketone (V),which is condensed with 2-(dimethylamino)ethylamine (VI) in pyridine at 100 C giving the aminoketone (VII).Finally,this compound is demethylated with concentrated HBr in refluxing acetic acid.
参考文献标题:TAS-103
文献作者:Castar,J.; Hoshi,A.
参考来源:Drugs Fut 1998,23(5),513
产品链接: CAS No. 174634-09-4›› 产品链接: CAS No.174634-08-3››