Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine

Abstract

Schiff bases derived from 4-aminoantipyrine and vanillin were evaluated for their potential as antibacterial agents against some Gram positive and Gram negative bacterial strains. The antibacterial activity was studied against P. pseudoalcaligenes ATCC 17440, P. vulgaris NCTC 8313, C. freundii ATCC 10787 E. aerogenes ATCC 13048, S. subfava NCIM 2178 and B. megaterium ATCC 9885. The determination of the antibacterial activity was done using the Agar Ditsh method. The Schiff bases produced were: (1) 4-(4-hydroxy 3-methoxybenzylideneamino) -1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VV1]; (2) 4-(benzylideneamino) -1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VY2]); (3) 4-[(furan-3-ylmethylene) amino ]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VY3]?; (4) 4-(4-methoxybenzylideneamino) -1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VY4]?; (5) 2-methoxy-4-[(4-methoxyphenylimino) methyl ]phenol [VY5]; (6) 4-[(2,4-dimethylphenylimino) methyl]-2-methoxyphenol [VY6]); (7) 2-methoxy-4-(naphthalene-1-yliminomethyl) phenol [VY7]?and (8) 4-[(4-hydroxy-3-methoxybenzylidene)amino]-N-(5-methylisoxazol 3-yl)benzenesulfonamide [VY8]. The antibacterial activity was evaluated in two polar solvents, DMSO and DMF. The Schiff bases derived from vanillin as the central molecule with 2,4-dimethylaniline and sulphamethoxazole as the side chain in DMSO effectively inhibited the investigated bacteria and appear to be promising antimicrobial agents.

Studies on DNA cleavage and antimicrobial screening of transition metal complexes of 4-aminoantipyrine derivatives of N2O2 type

“…These compounds are readily hydrolyzed under acidic conditions leading to active aldehydes which can act as alkylating agents [4]. Besides, several azomethines have been reported to possess remarkable antibacterial [5][6][7][8][9], antifungal [10][11][12], anticancer [13][14][15][16] and diuretic activities [17]. Antibiotics such as Streptomycin, Aspergillic acid, Usnic acid and Tetracycline are known to have chelating properties.…”

Synthesis, spectral, thermal behaviors, and antimicrobial studies of some nanostructure five coordinated Hg(II) complexes

“…In general two important parameters are impressive, lipophilicity of compounds and characteristics of microorganism cell membrane in steric and electronic structure. An increase in lipid solubility and decrease in the polarity leads to easier transduction into the plasma membrane and finally more effective block of the active site of enzyme of microorganisms that disorder the respiration process of the cell preventing the growth of the microorganism [40,41]. This entire situation appears by attaching the ligand to mercury ion.…”

Synthesis, Structural Characterization and Anti-bacterial Activity of some Novel Schiff base Ligands and their Vanadium (IV) Metal Complexes

“…Streptomycin (100 ìg/ml/disc) was used as standard for anti-bacterial activitiy. A comparison of antibacterial activity of the synthesized compounds with that of standard drugs was effectively [24][25][26][27] presented in Table 7. In this study, all the synthesized compounds were evaluated for their in vitro antibacterial activity against two bacterias namely E.coli and B. subtiles.…”