<abstract xmlns="http://www.w3.org/1999/xhtml"><p>Synthesis of ethyl 7-hydroxy-1-azacoumarin-3-carboxylate (<bold>3</bold>) 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 <italic>N</italic>-substituted-7-hydroxy-1-azacoumarin-3-carboxamides (7-Hydroxy -1-azacoumarin-3-carboxamide (<bold>4</bold>) and <italic>N</italic>-phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide (<bold>5</bold>)). Bromo derivative (<italic>N</italic>-phenyl 6, 8-dibromo-7-hydroxy-1-azacoumarin-3-carboxamide (<bold>6</bold>)) was obtained from halogenation of compound <italic>N</italic>-phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide (<bold>5</bold>) with bromine in glacial acetic acid. <italic>N</italic>-phenyl-2,5-diacetoxy-6, 8-disubstituted-Quinoline-3-carboxamides (<italic>N</italic>-phenyl 2,7-diacetoxy-Quinoline-3-carboxamide (<bold>7</bold>) and <italic>N</italic>-phenyl 2,7-diacetoxy-6,8-dibromo-Quinoline-3-carboxamide (<bold>8</bold>)) were prepared via the acetylation of compounds 5 and 6 with acetic anhydride. Five compounds <bold>4–8</bold> were evaluated <italic>in vitro</italic> against more than one human tumor cell lines. Among the selected compounds, <bold>6</bold> showed the best <italic>in vitro</italic> cytotoxicity against the human cancer cell line; MCF-7 (with IC<sub>50</sub> = 10.12 μM). In addition, cell cycle analysis of compound <bold>6</bold> demonstrated cell cycle arrest at G2/M phase and Pre-G1 apoptosis.</p></abstract>

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 IC50 = 10.12 μM). In addition, cell cycle analysis of compound 6 demonstrated cell cycle arrest at G2/M phase and Pre-G1 apoptosis.

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

Polish Journal of Chemical Technology

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

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

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...

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

Published Online: May 05, 2021

Page range: 53 - 59

DOI: https://doi.org/10.2478/pjct-2021-0008

Keywords
azacoumarin-3-carboxamide, cytotoxicity, H, C-NMR spectra, MCF-7

© 2021 Safyah B. Bakare, published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

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

Published Online: May 05, 2021

Page range: 53 - 59

DOI: https://doi.org/10.2478/pjct-2021-0008

Keywordsazacoumarin-3-carboxamide, cytotoxicity, H, C-NMR spectra, MCF-7

© 2021 Safyah B. Bakare, published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Keywords
azacoumarin-3-carboxamide, cytotoxicity, H, C-NMR spectra, MCF-7