Novel aroylthioureas against Mycobacterium tuberculosis

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2025-06-03 DOI:10.1080/10426507.2025.2509703

Emine Kutlu (Conceptualization Investigation Methodology Writing – original draft) , Fatih Mehmet Emen (Conceptualization Data curation Formal analysis Funding acquisition Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing) , Muhammad Asim Ali (Conceptualization Formal analysis Investigation Methodology) , Ali Ihsan Karacolak (Conceptualization Formal analysis Investigation Methodology) , Tuncay Yesilkaynak (Conceptualization Formal analysis Investigation Methodology Writing – original draft) , Kübra Yıldırım (Conceptualization Formal analysis Investigation Methodology) , Cemilenur Ataş (Conceptualization Formal analysis Investigation Methodology) , Ece Şimşek (Conceptualization Formal analysis Investigation Methodology) , Ahmet Yılmaz Çoban (Conceptualization Formal analysis Investigation Methodology Writing – original draft Writing – review & editing)

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引用次数: 0

Abstract

In this study, N-([1,1′-biphenyl]-2-ylcarbamothioyl)-2-chlorobenzamide (L¹), N-([1,1′-biphenyl]-2-ylcarbamothioyl)furan-2-carboxamide (L²), N-((5-chloropyridin-2-yl)carbamothioyl)thiophene-2-carboxamide (L³) were synthesized and their structural characterizations were performed with FT-IR,¹H-NMR and ¹³C-NMR techniques. The crystal structure analysis of L³ was performed by single crystal X-ray diffraction method. Hirshfeld surface analyses and HOMO–LUMO energy level analyses were carried out for the L¹ and L³. The HOMO energies were calculated to be −0.21010 and −0.25281 eV, and the LUMO energies were −0.07204 and −0.17947 eV. Ionization and electron affinity values were also calculated. Newly synthesized thiourea derivatives were evaluated by nitrate reduction assay for anti-tuberculosis activity against 5 ATCC reference strains and 3 isolates of Mycobacterium tuberculosis with different resistance profiles. Among the synthesized derivatives, L³ did not show any anti-TB activity, while L¹ showed only low activity against ATCC 35837. Only the L² compound showed potent anti-TB activity against all M. tuberculosis strains tested. The L² compound has the potential to be a promising active agent against drug-resistant M. tuberculosis.

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抗结核分枝杆菌的新型芳基硫脲

本研究合成了N-（[1,1 ' -联苯]-2-酰基氨基甲氧基）-2-氯苯酰胺（L1）、N-（[1,1 ' -联苯]-2-酰基氨基甲氧基）呋喃-2-羧酰胺（L2）、N-(（5-氯吡啶-2-酰基）氨基噻吩-2-羧酰胺（L3），并利用FT-IR、1H-NMR和13C-NMR技术对其结构进行了表征。采用单晶x射线衍射法对L3的晶体结构进行分析。对L1和L3进行了Hirshfeld表面分析和HOMO-LUMO能级分析。HOMO的能量分别为- 0.21010和- 0.25281 eV， LUMO的能量分别为- 0.07204和- 0.17947 eV。还计算了电离值和电子亲和值。采用硝酸还原法评价新合成的硫脲衍生物对5株ATCC参考菌株和3株不同耐药谱的结核分枝杆菌的抗结核活性。合成的衍生物中，L3对ATCC 35837无抗结核活性，L1对ATCC 35837仅表现出较低的抗结核活性。只有L2化合物对所有结核分枝杆菌株表现出有效的抗结核活性。L2化合物有潜力成为一种有前途的抗耐药结核分枝杆菌的活性剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.