【药物名称】BMS-247615, TAS-103
化学结构式(Chemical Structure):
参考文献No.28317
标题:Novel fused indan deriv. and pharmaceutically acceptable salt
作者:Okazaki, S.; Asao, T.; Wakida, M.; Ishida, K.; Washinosu, M.; Utsugi, T.; Yamada, Y. (Taiho Pharmaceutical Co., Ltd.)
来源:EP 0713870; US 5710162; US 5733918; WO 9532187
合成路线图解说明:

Racemic lometrexol has been prepared.

合成路线图解说明:

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No.435717
标题:Synthesis of novel indeno[2,1-c]quinolin-7-one derivatives and their topoisomerase inhibitory and antitumor activities
作者:Ishida, K.; Wakida, M.; Utsugi, T.; Okazaki, S.; Yamada, Y.; Asano, T.
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.
合成路线图解说明:

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No.457489
标题:TAS-103
作者:Casta馿r, J.; Hoshi, A.
来源:Drugs Fut 1998,23(5),513
合成路线图解说明:

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.

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