Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases

Abstract

a b s t r a c tThe condensation of substituted aromatic aldehydes with 7-amino-4-methyl-quinolin-2(1H)-one (1) has lead to the isolation of quinolin-2(1H)-one derived Schiff bases (2-14). The copper(II) complexes (2a-14a) of the ligands were also prepared, and together with their corresponding free ligands were fully characterised by elemental analyses, spectral methods (IR, 1 H and 13 C NMR, AAS, UV-Vis), magnetic and conductance measurements. The bidentate ligands coordinated to the copper(II) ion through the deprotonated phenolic oxygen and the azomethine nitrogen of the ligands in almost all cases. X-ray crystal structures of two of the complexes, 5a and 8a, confirmed the bidentate coordination mode. All of the compounds were investigated for their antimicrobial activities against the fungus, Candida albicans, and against Gram-positive and Gram-negative bacteria. The compounds were found to have excellent antiCandida activity but were inactive against Staphylococcus aureus and Escherichia coli. Selected compounds (2-8 and 2a-8a) were also screened for their in vitro anticancer potential using the human hepatic carcinoma cell line, Hep-G 2 . Several derivatives were shown to be active comparable to that of cisplatin.

Schiff Bases: A Versatile Pharmacophore

“…Cisplatin was used as a standard drug for the comparison. Screened compounds were found to be active antifungal agents and compound (7E)-7-(3-ethoxy-2-hydroxybenzylideneamino)-4-methylquinolin-2(1H)-one was reported as a potent cytotoxic agent which enlightened the good potential of Cu(II) complexes of Schiff base ligands as therapeutic agents [46]. (Figure 30) was synthesized and evaluated for their in vitro antioxidant, anti-inflammatory, and antimicrobial activities.…”

Cu(II) Complexes of Isoniazid Schiff Bases: DNA/BSA Binding and Cytotoxicity Studies on A549 Cell Line

“…Schiff 's bases could be hydrolyzed selectively by the tumor cells to act as alkylating agents; at the same time the active amine becomes free to act as antimetabolite [1]. Studies show that the metal complexes of Schiff 's base ligands have better antimicrobial and anticancer activities as compared to Schiff 's bases [2].…”

Synthesis, Characterization, Antibacterial and DNA Binding Studies of Mn (II) Complex of 3-(2-(2-Hydroxy-3- Methoxybenzylidene) Hydrazinyl) Quinoxalin-(1H)-One

“…Transition metal complexes of Schiff base ligands are known for their potential applications in antibacterial, antifungal, magnetic, photoluminescent and DNA binding properties [1][2][3][4][5][6][7][8][9][10][11]. During recent years, quinoxaline based Schiff bases emerged as an important class of ligands and formed metal complexes with a broad spectrum of biological activity [12][13][14][15][16][17].Owing to the significant chemical, catalytic and biological activities of the Schiff base complexes, the present communication reports the synthesis, characterization and biological activity of Mn (II) complex of the Schiff base ligand, 3-(2-(2-hydroxy-3-methoxybenzylidene) hydrazinyl) quinoxalin-2(1H)-one (VHQO).…”