Fluorobenzylidene-1,2,4-triazol-3-one Derivatives: Synthesis, Characterization, Antimicrobial Activity, and Molecular Docking Study

IF 0.9 4区 化学 Q4 CHEMISTRY, ORGANIC
N. Süleymanoğlu, S. Utaş Cobuloğlu, F. Çelik, Y. Ünver, R. Ustabaş, H. İ. Güler, Ş. Direkel
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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 13 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).

Abstract Image

氟苄啶-1,2,4-三唑-3-酮衍生物:合成、表征、抗菌活性和分子对接研究
合成了一系列三种氟二酶-1,2,4-三唑-3-酮衍生物(E)-4-[(2-氟二酶-)氨基]-(1)、(E)-4-[(3-氟二酶-)氨基]-(2)和(E)-4-[(4-氟二酶-)氨基]-5-甲基-2,4-二氢- 3h -1,2,4-三唑-3-酮(3)),并用FTIR、1H和13C NMR对其进行了表征。在合成的三种异构体(E)-4-(氟乙基氨基)-5-甲基-2,4-二氢- 3h -1,2,4-三唑-3- 1衍生物中,异构体1和2是新化合物,化合物3是已知的。采用DFT/B3LYP/ 6-311 ++G(d,p)方法进行理论研究。对化合物1 ~ 3的分子结构进行了优化,并确定了其结构参数。实验FT-IR和NMR数据与计算值进行了比较,证实了分子结构,支持了实验结果。采用微量稀释法测定化合物1 ~ 3的抑菌活性和杀利什曼菌活性。肺炎链球菌是最敏感的细菌,而化合物2对被试细菌的效果不如其他衍生物。分子对接分析确定了化合物1抗利什曼原虫活性的关键分子相互作用,显示了对锥虫硫酮还原酶(TRe)的高结合亲和力。
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来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
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.
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