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Novel thiourea derivatives against Mycobacterium tuberculosis: synthesis, characterization and molecular docking studies
Phosphorus, Sulfur, and Silicon and the Related Elements ( IF 1.4 ) Pub Date : 2023-04-25 , DOI: 10.1080/10426507.2023.2201503
Emine Kutlu 1 , Fatih Mehmet Emen 1 , Kübra Yıldırım 2, 3 , Cemilenur Ataş 3, 4 , Ruken Esra Demirdogen 5 , Tuncay Yesilkaynak 6 , Neslihan Kaya Kinaytürk 7 , Ece Şimşek 2, 3, 4 , Ahmet Yılmaz Çoban 2, 3, 4
Affiliation  

Abstract

N-((2-chloropyridin-3-yl)carbamothioyl)thiophene-2-carboxamide (HL1), N-((6-methylpyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (HL2), N-(allylcarbamothioyl)thiophene-2-carboxamide (HL3), 2-chloro-N-(methyl(1-phenylethyl)carbamothioyl)benzamide (HL4) and 2-chloro-N-(bis((R)-1-phenylethyl)carbamothioyl)benzamide (HL5) were synthesized and characterized via FT-IR, 1H-NMR, 13C-NMR and HR-MS techniques and HL3 was characterized via a single crystal X-ray diffraction experiment. The antituberculosis activity of the synthesized thiourea derivatives was tested against the H37RV (ATCC27294), ATCC35822 (INH resistant), ATCC35838 (RIF resistant), ATCC35820 (STM resistant) and ATCC35837 (EMB resistant) standard bacteria strains. The thiourea derivatives were tested on two MDR and one primary drug-sensitive isolates with the microplate nitrate reductase test method. The results indicated that HL2 and HL3 had tuberculosis activity on some of the isolates. It was observed that HL4 was the most effective among all the thiourea derivatives. The interaction mechanism of the synthesized compounds on 2X23, a tuberculosis protein, was investigated via molecular docking method. The interaction was observed to occur over S and Cl atoms in all the compounds. The compounds containing the methyl group were observed to interact via this group.



中文翻译:

抗结核分枝杆菌的新型硫脲衍生物:合成、表征和分子对接研究

摘要

N -((2-氯吡啶-3-基)硫氨甲酰基)噻吩-2-甲酰胺 (HL 1 ), N -((6-甲基吡啶-2-基)硫甲酰基)噻吩-2-甲酰胺 (HL 2 ), N - (烯丙基硫代氨基甲酰基)噻吩-2-甲酰胺 (HL 3 )、2-氯-N- (甲基(1-苯乙基)硫代氨基甲酰基)苯甲酰胺 (HL 4 ) 和 2-氯-N- (((R)-1-苯乙基)合成硫代氨基甲酰基)苯甲酰胺(HL 5 )并通过FT-IR、 1 H-NMR、13 C-NMR和HR-MS技术进行表征, HL 3通过单晶X射线衍射实验对其进行了表征。合成的硫脲衍生物的抗结核活性针对 H37RV(ATCC27294)、ATCC35822(INH 耐药)、ATCC35838(RIF 耐药)、ATCC35820(STM 耐药)和 ATCC35837(EMB 耐药)标准菌株进行了测试。使用微孔板硝酸还原酶测试方法对两种 MDR 和一种主要药物敏感分离株测试了硫脲衍生物。结果表明,HL 2和HL 3对部分分离株具有结核活性。据观察,HL 4是所有硫脲衍生物中最有效的。通过分子对接方法研究了合成化合物与结核蛋白2X23的相互作用机制。在所有化合物中都观察到相互作用发生在 S 和 Cl 原子上。观察到含有甲基的化合物通过该基团相互作用。

更新日期:2023-04-25
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