Experimental synthesis, biological evaluation, theoretical investigations of some novel benzoxazolinone based Schiff under eco-environmental conditions as potential antioxidant agents

Houria Bentoumi (1) , Sourour Tliba (2) , Hacène K'Tir (1) , Djawhara Chohra (2) , Zineb Aouf (1) , Yasmina Adjeroud (2) , Aïcha Amira (1) , Rachida Zerrouki (3) , Malika Ibrahim-Ouali (4) , Nour Eddine Aouf (1) , Messaoud Liacha (2)

1 LAOC - Laboratory of Applied Organic Chemistry
2 UBMA - Université Badji Mokhtar [Annaba]
3 PEIRENE - PEIRENE
4 AMU - Aix Marseille Université

In this paper, we have developed a new, non-hazardous and eco-friendly access route for the synthesis of a novel Schiff bases containing 2-oxo-3H-benzoxazole scaffold 4(a-f) by lemon juice as natural catalyzed acid under solvent-free conditions. The chemical structures of the new synthesized compounds were elucidated on the basis of the FT-IR, 1 H and 13 C-NMR spectroscopic techniques and all molecules were isolated with moderate yields after shorter reaction times. Furthermore, a preliminary study on the in vitro antioxidant activity of some synthesized compounds was investigated. The biological activity results revealed that highest DPPH radical-scavenging activity was observed for compound 4e with an IC 50 of 2.13 μg.mL −1 , more active than the standard ascorbic acid (IC 50 = 2.16 μg.mL −1). In-silico studies based on density functional theory (DFT) were realized to rationalize the biological activity with the structural and electronic properties of the 6-imino-2-oxo-3H-benzoxazoles. We using the molecular docking simulation to study the affinity and the possible binding mode of complexed ligand-protein. The synthesized molecules were tested to cross the clinical test by the ADMET prediction, these results indicated that the compounds 4(a-f) have excellent drug-likeness properties.

Mots clés: Benzoxazolinone; Antioxidant evaluation; Nitric oxide synthase; NOS; DFT study; Molecular docking

Domaines: Chimie

Houria Bentoumi, Sourour Tliba, Hacène K'Tir, Djawhara Chohra, Zineb Aouf, et al.. Experimental synthesis, biological evaluation, theoretical investigations of some novel benzoxazolinone based Schiff under eco-environmental conditions as potential antioxidant agents. Journal of Molecular Structure, 2022, 1270, pp.133986. ⟨10.1016/j.molstruc.2022.133986⟩. ⟨hal-03961744⟩