Synthesis, characterization and application of chitosan conjugated heterocyclic compounds

Abstract

Derivatives of formyl pyrazole were synthesized by the reaction of acetophenone, 4-methyl acetophenone, 3-acetyl furan, 3-acetyl thiophen and phenyl hydrazine derivatives. The product was treated with Vilsmeier reagent producing different formyl pyrazole derivatives which were characterized by FT-IR, 1HNMR, Elemental analysis and Mass spectroscopy. The formyl pyrazole derivatives were reacted with chitosan to produce chitosan/ pyrazole Schiff base. These Schiff bases were characterized by FT-IR and TGA.The antimicrobial activity of chitosan/ pyrazol Schiff base (CSB) was evaluated against Gram-positive bacteria (Staphylococcus aureus and Bacillus cereus), gram negative bacterium (Escherichia coli) and fungus (Aspergillus niger). Results indicated agood inhibitory activity for CSB-14 when tested against B.cereus that gave inhibition zone of 7.5 ± 0.6 (mm), however CSB-18 gave a pronounced inhibitory activity against S. aureus and recorded 25 ± 2.0 (mm). All synthesized derivatives have no inhibitory activity against Gram negative E. coli. CSB-14, and CSB-15 exhibited inhibitory activity against tested A. niger that was used as a fungal model which gave 19 ± 0.9 and 18 ± 1.0 inhibition zone (mm) respectively. Thus, these results showed that, functionalization of chitosan with the hetero-cyclic compounds created biological activities of the synthesized derivatives; hence the synthesized pyrazole derivatives have not recorded any inhibitory activity before its immobilization onto chitosan.