Synthesis, spectroscopic characterization, reactive properties by DFT calculations, molecular dynamics simulations and biological evaluation of Schiff bases tethered 1,2,4-triazole and pyrazole rings

• DOI: 10.1016/j.molstruc.2018.09.037
• Publication Date: 2018-09-16T02:06:21Z
• Authors: Renjith Raveendra...; Khalid Karrouchi; Saad Fettach; Stevan Armaković; Sanja J. Armaković; Younes Brik; Jamal Taoufik; Smaail Radi; My El Abbes Faouzi; M'hammed Ansar
• Keywords: 01 natural sciences; 0104 chemical sciences

© 2018 Elsevier B.V. The synthesis, spectroscopic characterization, reactivity study and evaluation of antioxidant and α-glucosidase inhibitory activities of two Schiff bases containing 1,2,4-triazole and pyrazole rings namely: 4-((4-methoxybenzylidene)amino)-5-(5-methyl-1H-pyrazol-3-yl)-4H-1,2,4-triazole-3-thiol 3a and 4-((4-(dimethylamino)benzylidene)amino)-5-(5-methyl-1H-pyrazol-3-yl)-4H-1,2,4-triazole-3-thiol 3b were reported in the present work. Reactive properties of the two compounds have been investigated by means of combination of DFT calculations, molecular dynamics (MD) simulations and drug likeness parameters, followed by calculations of molecular electrostatic potential (MEP) and average local ionization energy (ALIE) values. Additionally, the sensitivity of 3a and 3b towards the autoxidation mechanism has been investigated by the concept of bond dissociation energies for hydrogen abstraction (H-BDE). α-glucosidase inhibition assay revealed that the two compounds displayed significant inhibitory potentials in terms of relative IC50 values as compared to that of the reference drug (Acarbose). In addition, the antioxidant activity of the synthesized compounds were determined in vitro by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) and ferric reducing antioxidant power (FRAP) methods. Results revealed that the compound 3a is a potent antioxidant agent.