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Indeno[1,2-b]pyridin-5-one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2023-11-21 , DOI: 10.1002/jhet.4759 Refaie M. Kassab 1 , Zeinab A. Muhammad 2 , Sami A. Al‐Hussain 3 , Magdi E. A. Zaki 3 , Mona H. Ibrahim 4 , Amani M. R. Alsaedi 5 , Thoraya A. Farghaly 6
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2023-11-21 , DOI: 10.1002/jhet.4759 Refaie M. Kassab 1 , Zeinab A. Muhammad 2 , Sami A. Al‐Hussain 3 , Magdi E. A. Zaki 3 , Mona H. Ibrahim 4 , Amani M. R. Alsaedi 5 , Thoraya A. Farghaly 6
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The prevalence of germs that are resistant to many antibiotics is rising rapidly the world over. There is a large group of researchers actively looking for better medicines. Here, we designed two series of hydrazonal and indeno[1,2-b]pyridin-5-one bearing hydrazone and azo-groups to test their antimicrobial activity. Molecular structures of all derivatives were assured based on their spectral data and elemental analyses. Results of the antimicrobial activity of the tested hydrazone and azo compounds showed promising potential for several derivatives. The minimum inhibitory concentrations (MICs) of hydrazones 4a-h and 6a-g displayed good antibacterial reactivities with a range of 3.91–250 μg/mL and moderate antifungal activity with a range of 15.6–500 μg/mL. The most promising hydrazone 4f and azo-6a compounds demonstrated MIC values against Streptococcus faecalis and Escherichia coli equal to 3.91 and 7.81 μg/mL, respectively. Moreover, azo compound 6a showed MIC value equal to 3.91 μg/mL against Enterobacter cloacae species. Additionally, derivative 4f exhibited a significant inhibitory profile against the E. coli gyrase A enzyme (IC50 = 5.53 μg/mL). On the other hand, compound 6a (IC50 14.05 μg/mL) exhibited the lowest DNA gyrase inhibitory activity as compared to compounds 4f and reference standard drug novobiocin, IC50 5.53 and 1.88 μg/mL, respectively. Pharmacokinetic and pharmacodynamic profiles and molecular docking studies for the two most promising molecules 4f and 6a were computed and revealed that both compounds have good ADME profiles and high binding affinity to DNA gyrase binding site.
中文翻译：
含有偶氮基团的茚并[1,2-b]吡啶-5-酮衍生物及其腙前体：合成、抗菌谱、DNA旋转酶结合亲和力和分子对接
对许多抗生素具有抗药性的细菌在世界范围内的流行率正在迅速上升。有一大群研究人员正在积极寻找更好的药物。在这里，我们设计了两个带有腙和偶氮基团的腙和茚并[1,2- b ]吡啶-5-酮系列来测试它们的抗菌活性。所有衍生物的分子结构均根据光谱数据和元素分析确定。测试的腙和偶氮化合物的抗菌活性结果显示了几种衍生物的良好潜力。腙4a - h和6a - g的最低抑菌浓度 (MIC)在 3.91–250 μg/mL 范围内表现出良好的抗菌活性，在 15.6–500 μg/mL 范围内表现出中等抗真菌活性。最有前途的腙4f和偶氮6a化合物对粪链球菌和大肠杆菌的 MIC 值分别为 3.91 和 7.81 μg/mL。此外，偶氮化合物6a对阴沟肠杆菌的 MIC 值为 3.91 μg/mL 。此外，衍生物4f对大肠杆菌促旋酶 A 酶表现出显着的抑制作用(IC 50 = 5.53 μg/mL)。另一方面，与化合物4f和参考标准药物新生霉素相比，化合物6a (IC 50 14.05 μg/mL)表现出最低的DNA旋转酶抑制活性，IC 50分别为5.53和1.88 μg/mL。对两种最有前途的分子4f和6a的药代动力学和药效学特征以及分子对接研究进行了计算，结果表明这两种化合物都具有良好的 ADME 特征和与 DNA 旋转酶结合位点的高结合亲和力。
更新日期：2023-11-26
中文翻译：
含有偶氮基团的茚并[1,2-b]吡啶-5-酮衍生物及其腙前体：合成、抗菌谱、DNA旋转酶结合亲和力和分子对接
对许多抗生素具有抗药性的细菌在世界范围内的流行率正在迅速上升。有一大群研究人员正在积极寻找更好的药物。在这里，我们设计了两个带有腙和偶氮基团的腙和茚并[1,2- b ]吡啶-5-酮系列来测试它们的抗菌活性。所有衍生物的分子结构均根据光谱数据和元素分析确定。测试的腙和偶氮化合物的抗菌活性结果显示了几种衍生物的良好潜力。腙4a - h和6a - g的最低抑菌浓度 (MIC)在 3.91–250 μg/mL 范围内表现出良好的抗菌活性，在 15.6–500 μg/mL 范围内表现出中等抗真菌活性。最有前途的腙4f和偶氮6a化合物对粪链球菌和大肠杆菌的 MIC 值分别为 3.91 和 7.81 μg/mL。此外，偶氮化合物6a对阴沟肠杆菌的 MIC 值为 3.91 μg/mL 。此外，衍生物4f对大肠杆菌促旋酶 A 酶表现出显着的抑制作用(IC 50 = 5.53 μg/mL)。另一方面，与化合物4f和参考标准药物新生霉素相比，化合物6a (IC 50 14.05 μg/mL)表现出最低的DNA旋转酶抑制活性，IC 50分别为5.53和1.88 μg/mL。对两种最有前途的分子4f和6a的药代动力学和药效学特征以及分子对接研究进行了计算，结果表明这两种化合物都具有良好的 ADME 特征和与 DNA 旋转酶结合位点的高结合亲和力。
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