Synthesis and biological activities of some aryl (alkyl)azole derivatives

Aryl (alkyl) azole group compounds have antifungal, anticonvulsant and antibacterial activities. Inhibition of heme oxygenase, indolamine 2,3-dioxygenase-1, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes is evident in the literature. There are also reports that compounds containing this aryl (alkyl) azole group, which are currently used in fungal infections, and activate antioxidant systems in vivo. In this study, 2-(1H-1,2,4-triazole-1-yl)-1-(2,4-dichlorophenyl) ethanol and three new aromatic side chain ester derivatives were synthesized based on the aryl (alkyl) azole structure. Four imidazole derivatives based on the aryl (alkyl) azole structure which were synthesized in another study and molecules in this study were evaluated for AChE and BChE enzyme inhibition and antioxidant activities. While enzyme inhibition were evaluated with Ellman’s modified method, antioxidant activities were evaluated with DPPH and FRAP methods. In this study synthesized molecules’ structure were elucidated with IR, 1H-NMR, 13C-NMR and LC-MS spectral analysis. While no activity was observed in the 1,2,4-triazole derivatives both for enzyme inhibition and antioxidant activity, in the imidazole derivative compounds low activity for enzyme inhibition and DPPH radical scavenging activity was observed. In FRAP method there were no activity in imidazole derivatives. While IC50was more concentrated than 1000 μMfor imidazole, standard Galantamin’s IC50 value was21.30 and 37.03 μM for enzyme inhibition. For antioxidant activity, standard Gallic acid IC 50 was68.83 μM and imidazole derivatives IC50 were more concentrated than 1000 μM. The absence of activity of our compounds suggests that large structures such as the aromatic ring in the side chain may be effective in enzyme interaction. We plan to synthesize new derivatives bearing alkyl (saturated, unsaturated, halogen substituents, etc.) groups in the side chain in the aryl (alkyl) azole group compounds and evaluate AChE and BChE enzyme inhibition and antioxidant activities