Tổng hợp và cấu trúc dãy hợp chất azometin từ axit 5-amino-2-metoxi-4-(3-metylfuroxan-4-yl)phenoxyaxetic

Abstract

catalysts, medicine, crystal engineering, anti-corrosion agent. Many compounds contained furoxan ring, a nitric oxide (NO) releasing moiety, display a variety of biological activities, for example anti-inflammatory activity, the vasodilator activity and the inhibition of platelet aggregation. In recent years, several classes of hybrid compounds, obtained combining appropriate pharmacophoric groups with NO-releasing functions, have been described, such as NO-aspirin, NO-steroids and NO-guanidines, some of these compounds are now under clinical investigations. In this paper, 2-methoxy-4-(3-methylfuroxan-4-yl)-5-nitrophenoxyacetic acid (synthesized from eugenol) was reduced with Na₂S₂O₄ in NaOH to give 5-amino-2-methoxy-4-(3-methylfuroxan-4-yl)phenoxyacetic acid. The latter was used as key compound for synthesis of a series of 11 new azomethines containing furoxan ring by condensation with various aromatic aldehydes. The obtained azomethines (the yield of 45-69%) are crystalline solids with melting points of 126-235 ^oC. The structure of the azomethines was determined by analyzing their IR, ¹H NMR and MS for some compounds. All resonance signals in the ¹H NMR spectra of examined compounds were accurately assigned based on analyzing the spin-spin splitting patterns, for some compounds 2D NMR was also used.

Keywords. Azomethine, Schiff base, furoxan, eugenol.