Synthesis, characterization, and biological activity of novel 1,2,4-triazole moieties: Antileishmanial, antimicrobial effects, and molecular docking studies

SÜLEYMANOĞLU N., ÜNVER Y., Ustabaş R., ÇELİK F., GÜLER H. İ., Direkel Ş., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1314, 2024 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1314
  • Publication Date: 2024
  • Doi Number: 10.1016/j.molstruc.2024.138724
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Keywords: 1,2,4-triazole, Antimicrobial activity, DFT, IR and NMR spectroscopy, Leishmanicidal activity, Molecular docking study
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study; new 1,2,4-triazole derivatives, (E)-4-(((3-methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino) methyl)phenyl 4-methoxybenzoate (3a), (E)-4-(((3-benzyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino) methyl)phenyl 4-methoxybenzoate (3b) and (E)-4-(((3-(4-fluorobenzyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl) imino)methyl)phenyl 4-methoxy benzoate methoxy benzoate (3c) were synthesized and characterized by FTIR and NMR (1H- and 13C-) spectroscopic methods. Structural and spectral parameters were calculated by DFT/ B3LYP/6-311++G(d,p) methods. The newly synthesized compounds 3a-3c were evaluated for their antimicrobial activities against eight pathogenic microorganisms. Standard commercial drugs ampicillin and fluconazole were used as references for bacteria and yeast, respectively. The leishmanicidal activity of three different synthesized compounds against Leishmania infantum promastigotes was investigated using the microdilution method. In addition, the study attempted to investigate the interactions crucial for the antileishmanial activity of compound 3b by molecular docking analysis targeting trypanothione reductase (TRe).