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

• Autorzy: Bakare Safyah B.

Identyfikatory

DOI

10.2478/pjct-2021-0008

• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

azacoumarin-3-carboxamide; cytotoxicity; 1H; 13C-NMR; spectraMCF-7

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2021
• Tom: Vol. 23, nr 1
• Strony: 53--59
• Opis fizyczny: Bibliogr. 11 poz., rys., tab., wz.

Twórcy

autor

Bakare Safyah B.

• Faculty of Education Shaqra University Saudi Arabia

Bibliografia

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• 9. Ai, Y., Liang, Y.J., Liu, J.C., He, H.W., Chen, Y., Tang, C., Yang, G.Z. & Fu, L.W. (2012). Synthesis and in vitro anti-proliferative evaluation of pyrimido[5,4-c]quinoline-4-(3H)-one derivatives. Eur. J. Med. Chem., 47, 206–213. DOI: 10.1016/j. ejmech.2011.10.044.
• 10. Abdelhameid, M.K., Zaki, I., Mohammed, M.R. & Mohamed, K.O. (2020). Design, synthesis, and cytotoxic screening of novel azole derivatives on hepatocellular carcinoma (HepG2 Cells). Bioorg. Chem., 101, 103995. DOI: 10.1016/j. bioorg.2020.103995.
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Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).