[3+2] cycloaddition synthesis of new (nicotinonitrile‐chromene)‐based bis(pyrazole) hybrids as potential acetylcholinesterase inhibitors
Ahmed E. M. Mekky, Sherif M. H. Sanad
Abstract
Abstract A [3+2] cycloaddition protocol was used to prepare two series of (nicotinonitrile‐chromene)‐based bis(pyrazoles) in 82%–91% yields. The protocol involved the reaction of nitrilimines, which were generated in situ by the action of triethylamine on hydrazonoyl chlorides, with the respective (nicotinonitrile‐chromene)‐based bis(enaminone). At the concentrations tested, bis(pyrazole) linked to 1‐(4‐methoxyphenyl) and 3‐acetyl units had the best acetylcholinesterase and DPPH‐free radical inhibitory activity.
Topics & Concepts
ChemistryTriethylamineCycloadditionPyrazoleAcetylcholinesteraseCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisEnzymeSynthesis and biological activityOrganic Chemistry Cycloaddition ReactionsSynthesis and Biological Evaluation