In vitro antioxidant activities and in silico molecular docking studies of N-substituted oxime derivatives

SARI S., Kilic N., YILMAZ M.

STRUCTURAL CHEMISTRY, vol.34, no.2, pp.605-616, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 34 Issue: 2
  • Publication Date: 2023
  • Doi Number: 10.1007/s11224-022-01978-0
  • Journal Name: STRUCTURAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, INSPEC
  • Page Numbers: pp.605-616
  • Keywords: Oxime, Antioxidant, Reactive oxygen species, Molecular docking
  • Kocaeli University Affiliated: Yes

Abstract

New N-substituted oxime derivatives (5b, 5d-g, 5i-k, and 5m) and known compounds (5a, 5c, 5h, 5g, 5l, and 5n-q) were obtained by reacting phenyl and butyl oxime chloride analogs with aniline, piperazine derivatives, piperidine, and diethylamine. Structures of all new compounds were determined by H-1 NMR, C-13 NMR, HRMS, and FTIR methods. All compounds were evaluated in vitro for their antiradical activity and hydrogen peroxide scavenging activity. Compounds 5g, 5h, 5i, 5j, 5k, 5l, 5m, and 5p have shown good antiradical activities with EC50 values < 1 (conc. antiradical (mu M)/conc. DPPH (mu M)). Similar results were obtained in the peroxide scavenging activity tests. These results have shown that piperidine and butyl substitution greatly increases the antiradical activity of the oximes. Compounds 5l and 5m were found to be the best radical scavengers. In addition, molecular docking studies were performed for compounds (5a-q) against CP450 (CYP1A2), NADPH oxidase, and Xanthine oxidase to predict their antioxidant capabilities through ROS-producing enzyme inhibitions.