STUDY FOR THE PLANNING OF NEW OXADIAZOLES AND OXADIAZOLIL 2,3- ENOPYRANOSIDES WITH POWERFUL BIOLOGICAL ACTIVITIES (ANTITUMORAL, ANTIMICROBIAL, ANTIVIRAL)
Medicinal chemistry; 1,2,4-Oxadiazoles; 2,3-unsaturated O-glycosides; Biological activity.
Medicinal chemistry plays an important role in the search for new biologically active molecules and many classes of compounds that show promising activities in combating/controlling various diseases are heterocyclic compounds. Among the class of heterocyclic compounds, 1,2,4-Oxadiazoles and 2,3-unsaturated O-glycosides stand out due to their wide spectrum of applications, mainly in the pharmacological sector. And with the aim of obtaining new molecules with biological properties, the synthesis of 1,2,4-Oxadiazoles derived from ethyl glycolate ester and methyl lactate was carried out and additionally the synthesis of 2,3-unsaturated O-glycosides. Initially, the synthesis of arylamidoximes was carried out and these were obtained with yields between (30-95%), then the ethyl glycolate ester was synthesized with a yield of (50%) and the tri-O-acetyl-D-glucal with a yield (70%) and later the 1,2,4-oxadiazoles were synthesized with yields between (50-75%). In parallel, the 2,3-unsaturated O-glycosides were synthesized through the Ferrier rearrangement using tri-O-acetyl-D-glucal and 1,2,4-oxadiazoles as aglycone, then the 2,3-Unsaturated O-glycosides were subjected to basic hydrolysis reactions and provided the hydrolyzed products in yields ranging from 40-56%). Continuing, an allylic oxidation was carried out to produce the final compounds with yields ranging from 65-75% yield. Furthermore, the in silico study was carried out and the compounds analyzed showed good pharmacokinetic properties. All compounds were subjected to characterization by IR spectroscopy, 1H and 13C NMR and carrying out biological activities.