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Synthesis of ethyl 7-hydroxy-1-azacoumarin-3-carboxylate ( 3 ) was developed using ethyl-7-hydroxy coumarin-3-carboxylate and ammonium solution as the key synthons. Condensation of ethyl 7-hydroxy-1-azacoumarin-3-carboxylate with ammonium acetate and aniline to give  N -substituted-7-hydroxy-1-azacoumarin-3-carboxamides (7-Hydroxy -1-azacoumarin-3-carboxamide ( 4 ) and  N -phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide ( 5 )). Bromo derivative ( N -phenyl 6, 8-dibromo-7-hydroxy-1-azacoumarin-3-carboxamide ( 6 )) was obtained from halogenation of compound  N -phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide ( 5 ) with bromine in glacial acetic acid.  N -phenyl-2,5-diacetoxy-6, 8-disubstituted-Quinoline-3-carboxamides ( N -phenyl 2,7-diacetoxy-Quinoline-3-carboxamide ( 7 ) and  N -phenyl 2,7-diacetoxy-6,8-dibromo-Quinoline-3-carboxamide ( 8 )) were prepared via the acetylation of compounds 5 and 6 with acetic anhydride. Five compounds  4–8  were evaluated  in vitro  against more than one human tumor cell lines. Among the selected compounds,  6  showed the best  in vitro  cytotoxicity against the human cancer cell line; MCF-7 (with IC 50  = 10.12 μM). In addition, cell cycle analysis of compound  6  demonstrated cell cycle arrest at G2/M phase and Pre-G1 apoptosis.

polish journal of chemical technology

Anti-tumor agents: Design, Synthesis, and Biological study of <i>N</i>-Substituted-7-hydroxy-1-azacoumarin-3-carboxamide derivatives as potent cytotoxic agents

Anti-tumor agents: Design, Synthesis, and Biological study of N-Substituted-7-hydroxy-1-azacoumarin-3-carboxamide derivatives as potent cytotoxic agents