Biological Applications of Tryptamine Schiff Base Derivatives

Abstract

Abstract-We report the synthesis and biological applications of 4-{[2-(1H-Indol-3-yl)-ethylimino]-methyl} -benzene-1,3-diol (3a) and 4-{[2-(1H-Indol-3-yl)-ethylimino]-methyl}-3-methoxy-phenol (3b) Schiff base compounds derived from tryptamine. Tryptamine was refluxed in ethanol with 2,4-dihydroxybenzaldehyde and 4-hydroxy-2-methoxy-benzaldehyde and the resulting products were characterized using UV-VIS, FTIR, 1 H and 13 C NMR. Microdilution method was used to determine the bactericidal (against 14 strains) and fungicidal (against 7 strains) properties of the compounds. Spectroscopy data including NMR confirmed the successful condensation of tryptamine with the carbonyls. The compounds exhibited greater activity compared to commercial drugs used standards. All tested microorganisms were sensitive to the test compounds. Compound 3b exhibited better and broader spectrum activity than 3a with minimum fungicidal and bactericidal concentration (MFC) and (MIC) of 7.8 µg/mL against Aspergillus carbonarius, A. niger, Fusarium verticillioides, Escherichia coli, Staphylococcus epidermidis and Klebsiella oxytoca. Tryptamine Schiff bases could be good antimicrobial agents.