基于双噻唑通过 2-苯氧基-N-芳基乙酰胺基团连接到喹喔啉或噻吩并噻吩的新型混合分子支架：合成、抗菌活性和分子对接研究,ACS Omega

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基于双噻唑通过 2-苯氧基-N-芳基乙酰胺基团连接到喹喔啉或噻吩并噻吩的新型混合分子支架：合成、抗菌活性和分子对接研究
ACS Omega ( IF 3.7 ) Pub Date : 2023-11-10 , DOI: 10.1021/acsomega.3c07125
Mostafa E Salem _{1,

2} , Abbas H Abdullah ₂ , Nada S Ibrahim ₃ , Magdi E A Zaki ₁ , Ahmed H M Elwahy ₂ , Ismail A Abdelhamid ₂

Affiliation

微生物对抗菌药物的耐药性已经危及世界各地许多人的健康。克服耐药性问题需要发明具有新作用机制的分子，以免与现有疗法发生交叉耐药性。由于杂环化合物对多种革兰氏阳性和革兰氏阴性菌株具有强大的抗菌活性，因此对药物化学家来说是有吸引力的候选物。在这方面，作为独特的杂化化合物，我们合成了通过2-苯氧基-N-芳基乙酰胺部分与喹喔啉或噻吩并噻吩连接的新型双噻唑家族。通过使相关的双(α-卤代酮)与相应的缩氨基硫脲在乙醇中在回流下与几滴TEA反应来合成目标化合物。在可比较的反应条件下，通过使适当的双(缩氨基硫脲)与各自的α-卤代酮反应合成异构双(噻唑)。使用元素和光谱数据确认了新型化合物的结构。所有合成的化合物均进行了体外抗菌活性测试。化合物12a的抑菌圈宽度为12mm，对金黄色葡萄球菌的活性与对照药妥布霉素相同。化合物12b显示出20mg/mL的针对枯草芽孢杆菌的最小抑制浓度(MIC) 。一些合成的化合物通过针对两种细菌蛋白（二氢叶酸还原酶和酪氨酰-tRNA 合成酶）的分子对接进行了测试。

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Novel Scaffolds Based on Bis-thiazole Connected to Quinoxaline or Thienothiophene through 2-Phenoxy-N-arylacetamide Groups as New Hybrid Molecules: Synthesis, Antibacterial Activity, and Molecular Docking Investigations

The resistance of microorganisms to antimicrobials has endangered the health of many people across the world. Overcoming the resistance problem will require the invention of molecules with a new mechanism of action so that no cross-resistance with existing therapies occurs. Because of their powerful antibacterial activity against a wide spectrum of Gram-positive and Gram-negative bacterial strains, heterocyclic compounds are appealing candidates for medicinal chemists. In this regard, as unique hybrid compounds, we synthesized a novel family of bis-thiazoles linked to quinoxaline or thienothiophene via the 2-phenoxy-N-arylacetamide moiety. The target compounds were synthesized by reacting the relevant bis(α-haloketones) with the corresponding thiosemicarbazones in EtOH at reflux with a few drops of TEA. Under comparable reaction conditions, the isomeric bis(thiazoles) were synthesized by reacting the appropriate bis(thiosemicarbazone) with the respective α-haloketones. The structures of the novel compounds were confirmed using elements and spectral data. All of the synthesized compounds were tested for antibacterial activity in vitro. With an inhibitory zone width of 12 mm, compound 12a had the same activity as the reference medication tobramycin against Staphylococcus aureus. Compound 12b showed 20 mg/mL as a minimum inhibitory concentration (MIC) against Bacillus subtilis. Some of the synthesized compounds were tested via molecular docking against two bacterial proteins (dihydrofolate reductase and tyrosyl-tRNA synthetase).

更新日期：2023-11-10

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