Syntheses, Characterization, and Antibacterial Activities of Four New Schiff Base Compounds Derived from 1‐Phenyl‐3‐methyl‐4‐benzoyl‐2‐pyrazolin‐5‐one

Abstract

Four new Schiff bases were designed and synthesized. 5‐Methyl‐4‐(4‐aminophenylamino‐phenyl‐methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 1) and 5‐methyl‐4‐(2‐aminophenylamino‐phenyl‐methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 2) were synthesized by interaction of 1‐phenyl‐3‐methyl‐4‐benzoyl‐2‐pyrazolin‐5‐one (PMBP) with o‐ and p‐phenylenediamine, respectively; 4,4′‐(1,2‐phenylenebis(azanediyl)bis(phenylmethanylylidene))bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5(4H)‐one) (compound 3) and 5‐methyl‐4‐(phenyl(2‐((3‐phenylallylidene)amino)phenylamino)methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 4) were synthesized by interaction of compound 2 with PMBP and cinnamaldehyde in an ethanolic medium, respectively. The molecular structures of the title compounds were first characterized by single‐crystal X‐ray diffraction, mass spectrometry, and elemental analysis. The title compounds were tested for antibacterial activity (Escherichia coli, Staphylococcus aureus, and Bacillus subtilis) by disk diffusion method.

Apoptotic effect of novel pyrazolone-based derivative [Cu(PMPP-SAL)(EtOH)] on HeLa cells and its mechanism

“…A mixed-ligand copper complex [Cu(L)(phen)]·MeOH induced apoptosis in HeLa cells via accumulation of ROS 11 . Recent studies indicated that pyrazolone schiff base compounds might form novel metal complexes with metals such as platinum and copper, and these metal compounds exhibited better anti-tumor and antibacterial activities than pyrazolone 12 , 13 . In the initial stages of the present study, we synthesized a copper complex of the pyrazolone schiff base, called 1-phenyl-3-methyl-4-propionyl-5-pyrazolone-salicylic hydrazide-copper (II) complex [Cu(PMPP-SAL)(EtOH)].…”