W4R

Chemical Name: 7-Amino-6-chloro-10-[2-(diethylamino)ethyl]-1-hydroxy-3-methoxyacridin-9(10H)-one
项目整合开发状态: Biological Testing
项目研究机构: Mediolanum (Originator), Universit?degli Studi di Perugia (Originator)
合成路线:Ullman reaction of 2,4-dichloro-5-nitrobenzoic acid (I) with 3,5-dimethoxyaniline (II) in the presence of cupric acetate gave the diphenylamine carboxylic acid (III),which was cyclized with polyphosphoric acid at 110 C to afford acridone (IV).This was N-alkylated with 2-(diethylamino)ethyl chloride in the presence of 18-crown-6 to provide (V).The nitro group of (V) was then reduced to amine (VI) using SnCl2 and HCl.Finally,O-demethylation with boiling 48% HBr yielded the target monodemethylated compound along with the dihydroxyl analogue,which were separated by chromatography.

合成路线:Ullman reaction of 2,4-dichloro-5-nitrobenzoic acid (I) with 3,5-dimethoxyaniline (II) in the presence of cupric acetate gave the diphenylamine carboxylic acid (III),which was cyclized with polyphosphoric acid at 110 C to afford acridone (IV).This was N-alkylated with 2-(diethylamino)ethyl chloride in the presence of 18-crown-6 to provide (V).The nitro group of (V) was then reduced to amine (VI) using SnCl2 and HCl.Finally,O-demethylation with boiling 48% HBr yielded the target dihydroxy compound along with the monodemethylated analogue,which were separated by chromatography.