1-(3-甲基噻吩-2-基)-N-(3,4,5-三甲氧基苯基)甲亚胺:合成、光谱特性、抗利什曼病活性以及 DFT 和 In Silico 研究

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-11-07 DOI:10.1134/S1070428024090240
M. Evecen, F. Çelik, H. İ. Güler, Ş. Direkel, Y. Ünver
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引用次数: 0

摘要

以 3-甲基噻吩-2-甲醛和 3,4,5-三甲氧基苯胺为原料合成了 1-(3-甲基噻吩-2-基)-N-(3,4,5-三甲氧基苯基)甲亚胺(1,MTM),并通过傅立叶变换红外光谱、1H 和 13C NMR 光谱对其进行了表征。对标题化合物的几何结构进行了优化,并通过量子化学方法计算了其电子(FMO、NLO、MEP、NBO)、光谱(NMR、IR、UV)和热力学性质。计算得出的几何参数与实验得出的几何参数进行了比较。采用肉汤微稀释法测试了化合物 1 对婴儿利什曼原虫的杀利什曼活性,发现在所研究的浓度范围内,该化合物对婴儿利什曼原虫具有高效的杀利什曼活性。通过与锥硫蛋白还原酶(TRe)的分子对接分析,确定了导致抗利什曼病活性的可能相互作用。对接结果表明标题化合物具有很高的抑制常数,支持其抗利什曼病活性。
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1-(3-Methylthiophene-2-yl)-N-(3,4,5-trimethoxyphenyl)­methanimine: Synthesis, Spectroscopic Characterization, Antileishmanial Activity, and DFT and In Silico Studies

1-(3-Methylthiophen-2-yl)-N-(3,4,5-trimethoxyphenyl)methanimine (1, MTM) was synthesized from 3-methylthiophene-2-carbaldehyde and 3,4,5-trimethoxyaniline and characterized by FTIR and 1H and 13C NMR spectra. The geometric structure of the title compound was optimized, and its electronic (FMO, NLO, MEP, NBO), spectroscopic (NMR, IR, UV), and thermodynamic properties were calculated by quantum chemicial methods. The calculated and experimental geometric parameters were compared with each other. Compound 1 was tested for leishmanicidal activity against Leishmania infantum by the broth microdilution method and was found to be efficient against Leishmania infantum promastigotes in the concentration range studied. Possible interactions responsible for the antileishmanial activity were determined by molecular docking analysis against trypanothione reductase (TRe). The docking results demonstrated high inhibition constant of the title compound and supported its antileishmanial activity.

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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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