Synthesis of Schiff Bases Based on Chitosan and Heterocyclic Moiety: Evaluation of Antimicrobial Activity

Schiff bases of chitosan (CS) were prepared by reaction of four different heterocyclic compounds, namely, 1,3-dimethyl-2,4,6-trioxohexahydropyrimidine-5-carbaldehyde (M1), 3-acetyl-2H-chromen-2-one (M2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (M3), and 4-oxo-4H-chromene-3-carbaldehyde (M4), with CS using thermal and ultrasound approaches. CS Schiff base formation was confirmed by using FT-IR, XRD, and TGA. Characteristic data show that amino groups in chitosan reacted with the functional group in the heterocyclic compound to form the Schiff base. CS Schiff bases show thermal stability more than pure CS. The antimicrobial activity of Schiff bases was tested against +ve Gram bacteria and -ve Gram bacteria. The result shows that Schiff bases prepared by temperature and ultrasound methods possess high antimicrobial activity against +ve Gram bacteria and -ve Gram bacteria; in comparison, Schiff bases produced by the ultrasound method have higher antimicrobial activity. The Schiff base (CSM4U), prepared by the ultrasound method by reaction of CS with 4-oxo-4H-chromene-3-carbaldehyde, exhibited higher antimicrobial activity than Gentamicin as an antibacterial agent. The inhibition range caused by CSM4U was between 19 and 27 mm. Moreover, CSM4U also acted as an antifungal agent, causing an inhibition zone of 21 mm for both Candida albicans and Candida tropicalis, which was higher than that of Terbinafine.