New carbazol derivatives containing 1,2,4-triazole: Synthesis, characterization, DFT study, acetylcholinesterase activity and docking study

ÜNVER Y., SÜLEYMANOĞLU N., USTABAŞ R., GÜLER H. İ., BEKTAŞ E., İNAN BEKTAŞ K., ...More

JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol.99, no.10, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 99 Issue: 10
  • Publication Date: 2022
  • Doi Number: 10.1016/j.jics.2022.100690
  • Journal Name: JOURNAL OF THE INDIAN CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Analytical Abstracts, Chemical Abstracts Core, EMBASE, Index Chemicus (IC)
  • Keywords: Carbazol, Triazole, Synthesis, DFT, Acetylcholinesterase activity, Molecular docking study, BIOLOGICAL-PROPERTIES, MOLECULAR DOCKING, ANTIOXIDANT, ENERGY, AMINO, NMR
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Carbazol derivatives, 4-(((9-ethyl-9H-carbazol-3-yl)methylene)amino)-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one (3) and 5-benzyl-4-(((9-ethyl-9H-carbazol-3-yl) methylene) amino)-2,4-dihydro-3H-1,2,4-triazole-3-one (4), were synthesized. Compounds 3 and 4 were characterized by The Fourier transform infrared (FTIR), pro-ton and carbon-13 nuclear magnetic resonance (1H-and 13C-NMR) spectroscopic methods. Density Functional Theory (DFT) calculations for compounds 3 and 4 were performed at B3LYP/6-311++G(d,p) level. Optimized geometry, IR and NMR parameters of compounds 3 and 4 were obtained. The in vitro anti-acetylcholinesterase activity of the compounds were examinated. In addition, Compounds 3 and 4 were tested to determine possible interactions against human acetylcholinesterase by in silico analysis.