NSC-669967, BP-1
Chemical Name: 6-[2-(Dimethylamino)ethylamino]-8,11-dihydroxy-7H-benzo[e]perimidin-7-one
项目整合开发状态: Biological Testing
项目研究机构: Politechnika Gdanska (Originator)
合成路线:The cyclization of anthracenedione derivative (I) with formamide in refluxing dimethylacetamide (DMA) in the presence of NH4VO3 affords benzo[e]perimidinone derivative (II),whose benzyl groups are removed with TFA to yield (III).Intermediate (III) is finally heated with 2-(dimethylamino)ethylamine (IV) in N,N,N',N'-tetramethylethylenediamine and a small amount of water.Alternatively,the target product can be obtained as follows: Reduction of the nitro group of anthracenedione derivative (V) by means of hydrazine and Pd/C provides amine (VI),which is then cyclized with formamide in phenol to give (VII).The removal of the benzyl groups of (VII) by treatment with TFA yields intermediate (VIII),which is finally condensed with 2-(dimethylamino)ethylamine (IV) under similar conditions as described for (III).
📌 参考资料/链接：
参考文献标题:New derivs.of 6-[(aminoalkyl)amino]-7H-benzo[e]-perimidin-7-one,method of their preparation,and their use as a medicament
文献作者:Borowski,E.(Politechnika Gdanska)
参考来源:WO 9825910
📄 详细内容
合成路线:The cyclization of anthracenedione derivative (I) with formamide in refluxing dimethylacetamide (DMA) in the presence of NH4VO3 affords benzo[e]perimidinone derivative (II),whose benzyl groups are removed with TFA to yield (III).Intermediate (III) is finally heated with 2-(dimethylamino)ethylamine (IV) in N,N,N',N'-tetramethylethylenediamine and a small amount of water.Alternatively,the target product can be obtained as follows: Reduction of the nitro group of anthracenedione derivative (V) by means of hydrazine and Pd/C provides amine (VI),which is then cyclized with formamide in phenol to give (VII).The removal of the benzyl groups of (VII) by treatment with TFA yields intermediate (VIII),which is finally condensed with 2-(dimethylamino)ethylamine (IV) under similar conditions as described for (III).
参考文献标题:8,11-Dihydroxy-6-[8aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation
文献作者:Stefanska,B.; Dzieduszycka,M.; Bontemps-Gracz,M.M.; Borowski,E.; Martelli,S.; Supino,R.; Pratesi,G.; De Cesare,M.; Zunino,F.; Kusnierczyk,H.; Radzikowski,C.
参考来源:J Med Chem 1999,42(18),3494