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2,3-Dichloronaphthoquinone derivatives: Synthesis, antimicrobial activity, molecular modelling and ADMET studies
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2024-03-20 , DOI: 10.1016/j.bioorg.2024.107300 Hakan Kolancılar 1 , Hafize Özcan 2 , Ayşen Şuekinci Yılmaz 2 , Alparslan Semih Salan 3 , Abdulilah Ece 4
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2024-03-20 , DOI: 10.1016/j.bioorg.2024.107300 Hakan Kolancılar 1 , Hafize Özcan 2 , Ayşen Şuekinci Yılmaz 2 , Alparslan Semih Salan 3 , Abdulilah Ece 4
Affiliation
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In the present study, an intermediate namely 2-(3-bromopropylamino)-3-chloronaphthalene-1,4-dione was initially synthesized via the nucleophilic addition–elimination reaction between 2,3-dichloro-1,4-naphthoquinone and 3-bromo-1-aminopropane. Then a coupling reaction between the intermediate and piperazine derivatives yielded a number of 1,4-naphthoquinone derivatives. Spectroscopic analysis successfully characterized the products that were obtained in good yields. In vitro antibacterial properties of the compounds were examined against different bacterial strains. In vitro antibacterial properties of the compounds were examined against the bacterial strains and . While compound was found to be effective against all bacterial strains used, compound was active against three strains and compounds and were effective against the two. None of the compounds are effective against strain. molecular docking studies revealed that all compounds had docking scores comparable to the antibacterial drugs ciprofloxacin and gentamicin and might be considered as DNA gyrase B inhibitors. Molecular dynamics simulations were also conducted for a better understanding of the stability and the selected docked complexes. Additionally, the drug similarity of the synthesized compounds and ADMET characteristics were examined in conjunction with the antibiotic ciprofloxacin, and drug potentials were then evaluated. Compatible predictions were found with the drug similarity and ADMET parameters.
中文翻译：
2,3-二氯萘醌衍生物：合成、抗菌活性、分子建模和 ADMET 研究
在本研究中，通过2,3-二氯-1,4-萘醌与3-二氯萘醌之间的亲核加成-消除反应，初步合成了中间体2-(3-溴丙氨基)-3-氯萘-1,4-二酮。溴-1-氨基丙烷。然后该中间体与哌嗪衍生物发生偶联反应，生成多种1,4-萘醌衍生物。光谱分析成功地表征了以良好产率获得的产物。检查了化合物针对不同细菌菌株的体外抗菌特性。检查了化合物对细菌菌株和 的体外抗菌特性。虽然发现该化合物对所用的所有细菌菌株均有效，但该化合物对三种菌株和化合物均具有活性，并且对两种菌株均有效。这些化合物都不能有效对抗应变。分子对接研究表明，所有化合物的对接分数与抗菌药物环丙沙星和庆大霉素相当，可能被视为 DNA 旋转酶 B 抑制剂。还进行了分子动力学模拟，以更好地了解稳定性和所选的对接复合物。此外，还结合抗生素环丙沙星检查了合成化合物的药物相似性和 ADMET 特性，然后评估了药物潜力。通过药物相似性和 ADMET 参数找到了兼容的预测。
更新日期：2024-03-20
中文翻译：
2,3-二氯萘醌衍生物：合成、抗菌活性、分子建模和 ADMET 研究
在本研究中，通过2,3-二氯-1,4-萘醌与3-二氯萘醌之间的亲核加成-消除反应，初步合成了中间体2-(3-溴丙氨基)-3-氯萘-1,4-二酮。溴-1-氨基丙烷。然后该中间体与哌嗪衍生物发生偶联反应，生成多种1,4-萘醌衍生物。光谱分析成功地表征了以良好产率获得的产物。检查了化合物针对不同细菌菌株的体外抗菌特性。检查了化合物对细菌菌株和 的体外抗菌特性。虽然发现该化合物对所用的所有细菌菌株均有效，但该化合物对三种菌株和化合物均具有活性，并且对两种菌株均有效。这些化合物都不能有效对抗应变。分子对接研究表明，所有化合物的对接分数与抗菌药物环丙沙星和庆大霉素相当，可能被视为 DNA 旋转酶 B 抑制剂。还进行了分子动力学模拟，以更好地了解稳定性和所选的对接复合物。此外，还结合抗生素环丙沙星检查了合成化合物的药物相似性和 ADMET 特性，然后评估了药物潜力。通过药物相似性和 ADMET 参数找到了兼容的预测。
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