Synthesis, antioxidant activity, docking simulation, and computational investigation of novel heterocyclic compounds and Schiff bases from picric acid

Bayrak H., Fahim A. M., Yaylacı Karahalil F., Azafad I., Boyracı G. M., Taflan E.

Journal of Molecular Structure, vol.1281, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1281
  • Publication Date: 2023
  • Doi Number: 10.1016/j.molstruc.2023.135184
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Picric acid, Aromatic nitro compounds, Schiff base, Antioxidant activity, Docking investigation, DFT investigation, MICROWAVE-ASSISTED SYNTHESIS, MOLECULAR DOCKING, BIOLOGICAL EVALUATION, CRYSTAL-STRUCTURE, 1,2,4-TRIAZOLE, OXIDASE
  • Karadeniz Technical University Affiliated: Yes


In this elucidation, we used the available picric acid commercial for the synthesis of different heterocyclics such as carbothioamide and 1,3,4-oxadiazole and different Schiff bases derivatives. Furthermore, the synthesis route of 1,3,4-oxadiazole derivatives is known in literature but we used here an aprotic solvent without basic conditions. Moreover, all the synthesized compounds exhibited antioxidant capacity, total phenolic content (TPC), total flavonoid substance amount (TF), iron (III) reducing antioxidant power (FRAP), and DPPH radical scavenging activity. The compounds 5d, 5e, and 5f showed excellent activity in all of the TPC, TF, FRAP, and DPPH parameters compared to the standards used. In addition, it was determined from the statistical studies that compound 4a and 5b as TPC and TF content; compounds 5c, 5e, and 5f as TPC content, and compounds 5a, 5c, and 5g as TF content showed similar, good-moderate effectiveness compared to the standards used. Also the docking stimulation of synthesized compounds with different proteins PDBID:2CDU and PDBID: 3RP8 showed excellent binding energy with Schiff base compounds, in addition to the optimization of these heterocycles with DFT/B3LYP/6-31 basis and determination there physical descriptor's which indicated the activity of Schiff base with correlated with biological evaluation.