Síntese e avaliação do potencial anticolinesterásico de tiazolidin-4-onas tendo como precursor a 2- cicloexilmetilamina

Abstract

A new series of 1,3-thiazodidin-4-ones (5a-m) was synthesized using 2-cyclohexylethanamine, some benzaldehydes (R-PhCHO, onde R é igual a H; 2-OCH3; 2,5-OCH3; 2-Cl; 3-Cl; 4-Cl; 2-NO2; 3-NO2; 4-NO2; 2-F; 3-F; 4-F; CH3) and mercaptoacetic acid by a one-pot multicomponent reaction. Conventional thermal heating and microwave irradiation procedures were used, obtaining good general yields. The microwave reaction provided the products in shortest time, used less solvent, and showed similar yields to the conventional methodology. All compounds were identified and characterized by Gas Chromatography coupled with Mass Spectrometer (GC-MS) and Nuclear Magnetic Resonance (1H and 13C NMR). The functionalized thiazolidinones were designed without basic nitrogen in their structures and with a smaller carbon chain between the thiazolidin-4-one ring and the cyclohexane ring. Some compounds were selected for testing as inhibitors of the enzyme acetylcholinesterase (AChE), however, none of the tested compounds showed inhibition of AChE in both tissues of the cerebral cortex and the hippocampus. In conclusion, this work presents thirteen unpublished 1,3-thiazolidin 4-ones, obtained through 2 methodologies and the biological results suggest that, in comparison with previous work by the research group LaQuiABio, a basic nitrogen is essential for the inhibitory activity of AChE.