Synthesis And Anticancer Evaluation Of Substituted Aminoanthraquinones

Anti-tumour drugs of anthraquinones have been developed since Italy scientistDimarco,Arcamone and Bonadonna studied and approved the curative effect ofDaunorubicin and Adriamycin in 60s last century. At present, there are many breedsof anthraquinones anti-tumour drugs were applied in clinic. In this paper, a series ofsubstituted anthraquinones were designed and synthesized on the basis ofBio-reductive drugs (BDs') action mechanism.The compounds 1-[(3-chloro-2-hydroxypropyl)amino]-9,10-anthracenedione(â… ), 1-(2,3-epoxypropene)amino-9,10-anthracenedione (â…¡) and 1-[(2,3-dihydroxypropyl)amino]-9,10-anthracenedione (â…¢) were produced by the reaction of1-aminoanthraquinone with 3-chloro-1,2-epoxypropene. The substrate 2,3-dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione was substituted with alkyl-diamines, thenoxidized to produce 1,4-bis[(2-aminoethyl)amino]-5,8-dihydroxy-9,10-anthracenedione(â…£),1,4-bis[(2-aminopropyl)amino]-5,8-dihydroxy-9,10-anthracenedione(â…¤),and 1,4-bis [(2-methyl-2-aminoethyl)amino]-5,8-dihydroxy-9,10-anthracenedione(â…¥).The acylation of compoundâ…£with nicotinyl chloride gave 1,4-bis[2-(nicotinamino)acetamino]-5,8-dihydroxy-9,10-anthracenedione(â…§), Finally, 1,4-bis(2-chloroacetamino)-9,10-anthracenedione (â…¦) was prepared by the reaction of 1,4-diamino-9,10-anthracenedione with chloroacetyl chloride. All those compounds werecharacterized by IR and 1HNMR.Anti-tumour in vitro activity of the synthesized compounds aginst A549(humanlung carcinoma) cells, LoVo(human colonic carcinoma) cells and Hep-2(human throatcarcinoma) cells were studied in this paper. The results show that the compoundâ…¢exhibits certain effect on growth inhibition against LoVo cells and Hep-2 cells, thecompoundâ…£exhibits better effect on growth inhibition against A549 cells, and thecompoundâ…¤andâ…¥exhibit good growth inhibition against all the three cancer cells.