Synthesis, Crystal Structures, and Antibacterial Activity of a Series of Hydrazone Compounds Derived From 4-Methylbenzohydrazide

Abstract

A series of hydrazone compounds, 4-methyl-N'-(4-nitrobenzylidene)benzohydrazide methanol solvate (1), N'-(4-hydroxy-3-nitrobenzylidene)-4-methylbenzohydrazide dimethanol solvate (2), and N'-(3,5-dibromobenzylidene)-4-methylbenzohydrazide (3), derived from 4-methylbenzohydrazide with different benzaldehydes, were synthesized and characterized by physico-chemical methods and single crystal X-ray diffraction. Crystals of the compounds are stabilized by intermolecular hydrogen bonds, as well as π···π stacking interactions. Antibacterial activity of the compounds against Staphylococcus aureus, Escherichia coli, and Klebsielle pneumoniae strains was studied. Compounds 1 and 2 have moderate minimum inhibition concentration values on the tested bacteria strains. Compound 3, with the Br-substituent groups, showed the highest activity on the bacterial strains.

Different Schiff Bases—Structure, Importance and Classification

“…Hydrazones have uses, among others, as pesticides, insecticides, nematicides, rodenticides or plant-growth regulators [ 124 ].…”

Synthesis, characterization, and BSA binding studies of newfangled 2-phenylacetohydrazide derivatives

“…Trigonally hybridized nitrogen in the azomethine group has biological importance due to the presence of a lone pair of electrons in sp 2 hybridized orbital [ 13 ]. Hydrazones consist of two attached nitrogen atoms of different nature which separates them from other functional groups such as oximes and imines [ 14 ] and have a C N double bond which has conjugation with a terminal nitrogen atom. The physical and chemical properties of hydrazones depend upon these structural fragments.…”