The synthesis of 1-(2,4-dichlorophenyl)-2-(1H-triazole-1-yl)ethyl alcohol and its ester derivates and investigation of the biological activities of them

Molecules having triazole ring are attracted with the various new biological activities. Aryl(alkyl)azole group compounds have antifungal, anticonvulsant and antibacterial activities. It is also present in studies evaluating enzyme inhibition of heme oxygenase, inhibition of indolamine 2,3-dioxygenase-1 enzyme, inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. There are also reports that compounds containing this aryl(alkyl)azole group, which are currently used in fungal infections, also 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 are 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 are elucidated with IR, 1H-NMR, 13C-NMR and LC-Mass spectral analysis. While no activity was observed in the 1,2,4-triazole derivatives both for enzyme inhibition and antioxidant activity, low activity for enzyme inhibition and DPPH radical scavenging activity was observed in the imidazole derivative compounds. In FRAP method there were no activity in imidazole derivatives. While IC50 is bigger than 1000 µM concentration for imidazole, standard Galantamin's IC50 value is 21.30 and 37.03 µM for enzyme inhibition. For antioxidant activity, standard Gallic acid IC 50 is 68.83 µM and imidazole derivatives IC50 are bigger than 1000 µM concentration. 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.