Abstract
This study aims to investigate the effect of the 4-dimethylamino group on benzaldehyde in the synthesis of N’-(4-dimethylaminobenzylidene)-4-hydroxybenzohydrazide. This compound contains amino, azomethine, hydroxyl, and hydrazide functional groups, which are known to exhibit various biological activities, including antimicrobial and anticancer properties. The synthesis was carried out in two reaction steps using microwave irradiation. In the first step, methyl 4-hydroxybenzoate was reacted with hydrazine to obtain 4-hydroxybenzohydrazide. In the second step, 4-hydroxybenzohydrazide was reacted with 4-dimethylaminobenzaldehyde. The presence of the 4-dimethylamino group (in the para position) on benzaldehyde affects the reactivity of the carbonyl carbon atom, enhancing its role as an electrophile. The reaction yields of N’-benzylidene-4-hydroxybenzohydrazide and N’-(4-dimethylaminobenzylidene)-4-hydroxybenzohydrazide were 84% and 88%, respectively. The addition of the 4-dimethylamino group to the benzene ring of benzaldehyde increases the reactivity of the carbonyl carbon as an electrophile, thereby improving the reaction yield. The docking molecule study of the compounds shows antibacterial activity against the ENR inhibitor. The compound N’-(4-dimethylaminobenzylidene)-4-hydroxybenzohydrazide demonstrated antibacterial activity against Bacillus subtilis and Escherichia coli, with a minimum inhibitory concentration (MIC) of 7.8 ppm.