Synthesis, Antimicrobial, and Anticancer Activity of Novel Sugar Hydrazones and Schiff Bases Linked to C-Furyl Glycosides

Abstract

3-Carbohydrazide-5-C-(l,4-anhydro-β-D-erythro-tetrofuranosyl)-2-methylfuran underwent acid-catalyzed condensation reaction with some monosaccharides to form the corresponding C-furyl sugar hydrazone derivatives. Acetylation of the latter product with acetic anhydride at room temperature produced corresponding O-acylated sugar hydrazones in excellent yield. While C-furyl sugar hydrazones derivatives reacted under reflux with acetic anhydride undergo cyclization to produce the corresponding oxadiazolines in high yield. Further, 3-сarbohydrazide derivative condensed with some aromatic aldehydes afforded the corresponding sugar hydrazones. Evaluation of antimicrobial activity against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans showed that sugar hydrazones analogues were the highly active compounds and some of them showed the most promising inhibition activity against the microorganisms. The antitumor activity against breast cancer (MCF7) cell line also showed highly significant effect.