新产品编号:508331
Chemical Name: N,2-Bis[2-(dimethylamino)ethyl]-9-nitro-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamide dihydrochloride
CAS No. 220249-88-7
项目整合开发状态: Biological Testing
项目研究机构: Universit?degli Studi di Camerino (Originator)
合成路线:The Ullmann condensation between 2-chloro-5-nitrobenzoic acid (I) and 2-amino-4-chlorobenzoic acid (II) afforded the diaryl amine (III).Cyclization of (III) by treatment with POCl3 in refluxing xylene yielded a mixture of the desired acridine (IV) and minor amounts of its regioisomer (V).The isomeric mixture of acids (IV) and (V) was activated as the respective mixed anhydrides with ethyl chloroformate and subsequently condensed with N,N-dimethylethylenediamine (VI) to produce the corresponding amides.The required isomer (VII) was easily isolated from the mixture owing to its insolubility in the reaction solvent.Finally,the title pyrazoloacridine compound was prepared by condensation of (VII) with 2-(dimethylamino)ethyl hydrazine in 2-ethoxyethanol at 120 C.
📌 参考资料/链接：
参考文献标题:Pyrazolo-acridine derivs.having antitumour activity
文献作者:Matelli,S.; Polucci,P.; Antonini,I.(Universit?degli Studi di Camerino)
参考来源:WO 9906405
📄 详细内容
合成路线:The Ullmann condensation between 2-chloro-5-nitrobenzoic acid (I) and 2-amino-4-chlorobenzoic acid (II) afforded the diaryl amine (III).Cyclization of (III) by treatment with POCl3 in refluxing xylene yielded a mixture of the desired acridine (IV) and minor amounts of its regioisomer (V).The isomeric mixture of acids (IV) and (V) was activated as the respective mixed anhydrides with ethyl chloroformate and subsequently condensed with N,N-dimethylethylenediamine (VI) to produce the corresponding amides.The required isomer (VII) was easily isolated from the mixture owing to its insolubility in the reaction solvent.Finally,the title pyrazoloacridine compound was prepared by condensation of (VII) with 2-(dimethylamino)ethyl hydrazine in 2-ethoxyethanol at 120 C.
合成路线:The cyclization of the acridinonecarboxamide (I) with N-[2-(1-piperidinyl)ethyl]hydrazine (II) in 2-ethoxyethanol at 120 C gives the pyrazoloacridine (III) (1),which is cyclized with phosgene (IV) in chloroform at room temperature to afford the target pentacyclic compound.
参考文献标题:Synthesis,antitumor cytotoxicity,and DNA-binding of novel N-5,2-Di(omega-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl) acridine-5-carboxamides
文献作者:Antonini,I.; Polucci,P.; Magnano,A.; Martelli,S.
参考来源:J Med Chem 2001,44(20),3329