Characterization and Biological Evaluation of Structurally Modified Taurine using Benzaldehydes

Abstract

Four Schiff base compounds (1-4) were synthesized by the reaction of taurine and benzaldehyde characterized by methoxy substitution at different positions. The chemical structures of these new compounds were determined using IR, ¹H NMR, ¹³C NMR and ESI-MS spectra. They are potassium 2-{[1-(3,5-dimethoxy-phenyl)meth-(Z)-ylidene]amino}ethane sulfonic acid, potassium 2-{[1-(3,4,5-trimethoxy-phenyl)-meth-(Z)-ylidene]amino}ethane sulfonic acid, potassium 2-{[1-(2,5-dimethoxy-phenyl)meth-(Z)-ylidene]amino}ethane sulfonic acid and potassium 2-{[1-(2,4,5-trimethoxy-phenyl)meth-(Z)-ylidene]amino}ethane sulfonic acid. The cytotoxicity of these taurine benzaldehyde Schiff bases and the effects of taurine benzaldehyde Schiff bases on the contractility of isolated jejunal segment (IJS) were determined. The results showed that no cytotoxic effects on caco-2 cell lines were observed when the concentrations of taurine benzaldehyde Schiff bases were below 50,000 μM and compounds 1, 2 increased and compounds 3, 4 decreased the contractility of isolated jejunal segment, indicating that methoxy substitution in different positions of taurine benzaldehyde Schiff bases may modify its effects on the contractility of isolated jejunal segment.