ABSTRACT
Two series of novel 3-cyano-2-(2,3,4,6-tetra-O-acetyl-ß-D-glucopyranosyloxo) pyridines and 3-cyano-2-(2,3,5-tri-O-acetyl-ß-D-ribofuranosyloxy)-4-trifluromethyl-6-phenyl pyridine were synthesized using efficient microwave methods. The targeted compounds were obtained in high yields by reacting 2-(1H)-pyridone or its salt with activated sugars using SiO2 under solvent-free conditions. Ammonolysis of the resulted acetylated nucleosides produced 3-cyano-2-(ß-D-glucopyranosyloxo)-pyridines and 3-cyano-2-(ß-D-ribofuranosyloxy)-4-trifluoromethyl-6-phenyl pyridine. These new products were fully characterized using 1D and 2D NMR. These compounds were screened for their antibacterial activities against G(+) and G(-) bacteria and some found to exhibit better antibacterial activities than the control drug.
Subject(s)
Anti-Infective Agents/chemical synthesis , Bacteria/drug effects , Glucosides/chemistry , Nucleosides/chemical synthesis , Pyridines/chemistry , Ribose/analogs & derivatives , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Nucleosides/chemistry , Nucleosides/pharmacology , Pyridines/chemical synthesis , Pyridines/pharmacology , Ribose/chemistry , Silicon Dioxide/chemistry , Solvents/chemistryABSTRACT
A series of trifluoromethyl-substituted hexahydropyrimidine derivatives were efficiently synthesized in excellent yields via one-pot three-component reaction of aromatic aldehydes, ethyl trifluoroacetoacetate and thiourea(urea) in presence of p-toluenesulfonic acid under solvent-free conditions at room temperature by grinding. The present method does not involve any hazardous organic solvent and has proven to be simple, efficient, environmentally benign and cost-effective compared with the classical synthetic methods. These compounds were screened for their antibacterial activities against Escherichia coli and Bacillus thuringiensis and found to exhibit remarkably better antibacterial activities than the control drug.
