Facile preparation of 6-chloro-9-amino-2-hydroxyacridine, a urinary metabolite of quinacrine and quinacrine mustard.
6-Chloro-9-amino-2-hydroxyacridine was found to be a metabolite of both quinacrine and the antimalarial alkylating agent quinacrine mustard. Its structure was confirmed by a one-step reaction of quinacrine with 48 percent hydrobromic acid. The presence of this compound as a metabolite of quinacrine mustard suggests a possible in vivo activation mechanism for its antitumor activity and a pharmacological basis for its toxicity to the liver. In vitro experiments showed that this new compound does react with chromosomes and, therefore, can be both a useful chromosome stain and an intercalating agent.
D000166:Acridines / Q000138:chemical synthesis / Q000378:metabolism*; D000818:Animals; D002875:Chromosomes / Q000648:ultrastructure; D011796:Quinacrine / Q000031:analogs & derivatives* / Q000378:metabolism*; D011797:Quinacrine Mustard / Q000378:metabolism; D051381:Rats; D013194:Staining and Labeling
D000166:Acridines; D011797:Quinacrine Mustard; D011796:Quinacrine