N-[(N-halogenoacyl)imino]acenaphthene-quinoxalines as potential antitumoral agents.
Applying a reaction formerly studied by the Authors between acenaphthenequinone and N1-(2-amino)phenyl-N2-acylhydrazines, a group of N-[(N-alpha- and beta- halogenoacyl)imino]acenaphthenequinoxalines were obtained. On account of the reactivity of the halogen atom, they are potentially interesting as antitumoral agents. In contrast with the beta-chloropropionyl derivative, the alpha-halogenoacyl derivatives were formed in low yields and with the simultaneous loss of the whole halogenoacylimino group. Thus, an alternative synthetic route was set up, consisting in the N-imination of acenaphthenequinoxalines by means of O-mesitylenesulfonylhydroxylamine, followed by acylation of the intermediate N-iminoacenaphthenequinoxalines. The National Cancer Institute of Bethesda evaluated the activity against lymphocytic leukemia P 388 on some of the numerous compounds now described. Only the N-chloroacetyliminoacenaphthenequinoxaline exhibited, at the dose of 50 mg/Kg i.p., 35% increase of the average survival time of treated mice. All the remaining compounds were inactive.
Boido
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Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Vazzana
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Sparatore
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D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet
D000970:Antineoplastic Agents; D011810:Quinoxalines