N. Süleymanoğlu, S. Utaş Cobuloğlu, F. Çelik, Y. Ünver, R. Ustabaş, H. İ. Güler, Ş. Direkel
{"title":"Fluorobenzylidene-1,2,4-triazol-3-one Derivatives: Synthesis, Characterization, Antimicrobial Activity, and Molecular Docking Study","authors":"N. Süleymanoğlu, S. Utaş Cobuloğlu, F. Çelik, Y. Ünver, R. Ustabaş, H. İ. Güler, Ş. Direkel","doi":"10.1134/S1070428025600238","DOIUrl":null,"url":null,"abstract":"<p>A series of three fluorobenzylidene-1,2,4-triazol-3-one derivatives―(<i>E</i>)-4-[(2-fluorobenzylidene)amino]- (<b>1</b>), (<i>E</i>)-4-[(3-fluorobenzylidene)amino]- (<b>2</b>), and (<i>E</i>)-4-[(4-fluorobenzylidene)amino]-5-methyl-2,4-dihydro-3<i>H</i>-1,2,4-triazol-3-one (<b>3</b>)―were synthesized and characterized by FTIR and <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. Of the three synthesized isomeric (<i>E</i>)-4-(fluorobenzylideneamino)-5-methyl-2,4-dihydro-3<i>H</i>-1,2,4-triazol-3-one derivatives, isomers 1 and 2 are novel compounds, and compound 3 is previously known. A theoretical study was performed using the DFT/B3LYP/6–311++G(d,p) method. The molecular structures of compounds 1–3 were optimized, and their structural parameters were determined. Experimental FT-IR and NMR data were compared with calculated values, which confirmed the molecular structures and supported the experimental findings. The antibacterial and leishmaniacidal activities of compounds <b>1</b>–<b>3</b> were evaluated by the microdilution assay. <i>Streptococcus pneumoniae</i> was the most susceptible bacterium, while compound 2 was less effective against the tested bacteria than the other derivatives. Molecular docking analysis identified key molecular interactions responsible for the antileishmanial activity of compound <b>1,</b> demonstrating a high binding affinity for <i>Trypanothione reductase</i> (TRe).</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"61 8","pages":"1479 - 1491"},"PeriodicalIF":0.9000,"publicationDate":"2025-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428025600238","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A series of three fluorobenzylidene-1,2,4-triazol-3-one derivatives―(E)-4-[(2-fluorobenzylidene)amino]- (1), (E)-4-[(3-fluorobenzylidene)amino]- (2), and (E)-4-[(4-fluorobenzylidene)amino]-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (3)―were synthesized and characterized by FTIR and 1H and 13C NMR spectroscopy. Of the three synthesized isomeric (E)-4-(fluorobenzylideneamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives, isomers 1 and 2 are novel compounds, and compound 3 is previously known. A theoretical study was performed using the DFT/B3LYP/6–311++G(d,p) method. The molecular structures of compounds 1–3 were optimized, and their structural parameters were determined. Experimental FT-IR and NMR data were compared with calculated values, which confirmed the molecular structures and supported the experimental findings. The antibacterial and leishmaniacidal activities of compounds 1–3 were evaluated by the microdilution assay. Streptococcus pneumoniae was the most susceptible bacterium, while compound 2 was less effective against the tested bacteria than the other derivatives. Molecular docking analysis identified key molecular interactions responsible for the antileishmanial activity of compound 1, demonstrating a high binding affinity for Trypanothione reductase (TRe).
期刊介绍:
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.