New thiazole, pyridine and pyrazole derivatives as antioxidant candidates: synthesis, DFT calculations and molecular docking study

Yassine Kaddouri; Farid Abrigach; El Bekaye Yousfi; Mohamed El Kodadi; Rachid Touzani

doi:10.1016/j.heliyon.2020.e03185

New thiazole, pyridine and pyrazole derivatives as antioxidant candidates: synthesis, DFT calculations and molecular docking study

Heliyon. 2020 Jan 9;6(1):e03185. doi: 10.1016/j.heliyon.2020.e03185. eCollection 2020 Jan.

Authors

Yassine Kaddouri¹, Farid Abrigach¹, El Bekaye Yousfi², Mohamed El Kodadi^{1

3}, Rachid Touzani¹

Affiliations

¹ Laboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohamed First University, Oujda, Morocco.
² Instituts Supérieurs des Professions Infirmières et Techniques de Santé (ISPITS), Hopital Al Farabi, Oujda, Morocco.
³ CRMEF Oriental, Centre Régional des Métiers de l'Education et de Formation Oujda, Morocco.

Abstract

Novel heterocyclic compounds containing pyrazole, thiazole and pyridine moieties were designed and prepared based on the condensation reaction between 1,3-thiazole or aminopyridine derivatives and 1H-pyrazole,3,5-dimethyl-1H-pyrazole or 1,2,4-triazole. Their structures were confirmed with FTIR, ¹H and ¹³C NMR analyses. DPPH scavenging assay was used to evaluate their antioxidant potential. The ligand 4 showed the best antioxidant activity with an IC₅₀ = 4.67 μg/mL, while IC₅₀ values of the other compounds were found to be ranging from 20.56 to 45.32 μg/mL. DFT and molecular docking studies were performed in order to gain better insights and to understand the relationship between the structures of the studied compounds and their antioxidant activities. The results obtained revealed a good agreement between the experimental and the theoretical findings.

Keywords: 1,3-Thiazole; Antioxidant activity; DFT; DPPH; Docking; Organic chemistry; Pharmaceutical chemistry; Phenol; Pyridine; Theoretical chemistry.