Synthesis and biological evaluation of some hybrid 2-quinolinone derivatives containing cinnamic acid as anti-breast cancer drugs

Abstract

ABSTRACT. A new series of hybrid 2-quinolinone derivatives were synthesized by using 7-hydroxy-4-methyl-1-amino-quinolin-2-one (2) and cinnamic acid. Hybrid halogenated 2-quinolinone derivatives (3-(7-hydroxy-4-methyl-3,6,8-tribromo-2-oxo-2H-quinolin-1-ylamino)-3-phenyl acrylic acid (4) and 3-(7-acetoxy-4-methyl-3,6,8-tribromo-2-oxo-1H-quinolin-1-ylamino)-3-phenyl acrylic acid (7)) were prepared via the halogenation of 3-(7-hydroxy-4-methyl-2-oxo-2H-quinolin-1-ylamino)-3-phenyl acrylic acid (3) with bromine to give compound 4 with acetic anhydride led to the formation of hydride halogenated 2-quinolinone derivative (7). All the synthesized hybrid 2-quinolinone and hybrid halogenated 2-quinolinone derivatives were tested for their cytotoxicity against MCF-7 cell line. DNA flow cytometric analysis of compounds 3 showed cell cycle arrest at G₂/M phase with concomitant increase of cells in apoptotic phase. Dual annexin-V/propidium iodide staining assay of compound 3 revealed that, the selected molecule increases the apoptosis of MCF-7 cells more than control.

KEY WORDS: Quinolinone, Hybrid, Cinnamic acid, Apoptosis, MCF-7 cells

Bull. Chem. Soc. Ethiop. 2021, 35(3), 551-564.

DOI: https://dx.doi.org/10.4314/bcse.v35i3.7