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

• Published in: Journal of molecular structure 2024-10, Vol.1314, p.138724, Article 138724
• Main Authors: Süleymanoğlu, Nevin, Ünver, Yasemin, Ustabaş, Reşat, Çelik, Fatih, Güler, Halil İbrahim, Direkel, Şahin, Bektaş, Kadriye İnan
• Format: Article
• Language: English
• Subjects: 1,2,4-triazole; Antimicrobial activity; DFT; IR and NMR spectroscopy; Leishmanicidal activity; Molecular docking study
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2024.138724

•The new 1,2,4-triazole compounds (3a–3c) was synthesized.•The molecular structures of the compounds were confirm by FTIR and NMR (1H- and 13C-) methods.•The calculations were performed at DFT/B3LYP/6-311++G(d,p) level.•In vitro antimicrobial activity was determined by microdilution broth method added Alamar blue.•Molecular docking analysis targeting trypanothione reductase (TRe) was conducted for compound 3b. 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).