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