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Synthesis of some novel N5‐sulfonylated and N1‐alkyated pyrazole derivatives and their antimicrobial activity in conjunction with molecular docking study
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-01-21 , DOI: 10.1002/jhet.3895 Nadia H. Metwally 1 , Eman A. Ragab 1 , Mona S. Mohamed 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-01-21 , DOI: 10.1002/jhet.3895 Nadia H. Metwally 1 , Eman A. Ragab 1 , Mona S. Mohamed 1
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Some novel N5‐sulfonylated 4 were synthesized via sulfonylation of 5‐amino‐1H‐pyrazole derivative 1 with arylsulfonyl chlorides. On the other hand, N1‐alkylated pyrazoles 7 and 10 were synthesized through alkylation of compound 1 with each of chloroacetamides and ethylchloroacetate under different conditions. Condensation of compounds 4 and 7 with different aromatic aldehydes furnished the corresponding arylidene derivatives. In spite of, condensation of 10 with aromatic aldehydes afforded the 2‐(5‐amino‐2‐aryl‐1H‐pyrazol‐1‐yl)acetic acid. The structure of the newly synthesized compounds was elucidated by elemental analyses and spectral data. Also, the suggested mechanisms for their formation were studied. Additionally, some selected new compounds were screened against antimicrobial activity. Compound 7c exhibited a higher activity against Candida albicans (inhibition zone diameter [IZD] = 31.3 ± 0.6 mm) than the standard antibiotic Nystatin (IZD = 21 ± 0.5 mm). Also, compound 7c showed minimum inhibitory concentration = 125 and 250 μg/mL against Klebsiella pneumonia and Staphylococcus aureus, respectively. Molecular docking study also was carried out for compound 7c.
中文翻译：
结合分子对接研究一些新型的N5磺化和N1烷基化的吡唑衍生物及其抗菌活性
通过5-氨基-1 H-吡唑衍生物1与芳基磺酰氯的磺酰化反应合成了一些新颖的N 5-磺酰化4。另一方面，通过在不同条件下分别用氯乙酰胺和氯乙酸乙酯将化合物1烷基化，可以合成N 1-烷基化的吡唑7和10。化合物4和7与不同的芳族醛的缩合提供了相应的亚芳基衍生物。尽管如此，将10与芳族醛缩合仍可得到2-（5-氨基-2-芳基-1 H-吡唑-1-基）乙酸。通过元素分析和光谱数据阐明了新合成化合物的结构。此外，研究了其形成的建议机制。此外，针对抗微生物活性筛选了一些选定的新化合物。与标准抗生素制霉菌素（Nystatin）（IZD = 21±0.5 mm）相比，化合物7c对白色念珠菌具有更高的活性（抑制区直径[IZD] = 31.3±0.6 mm）。此外，化合物7c对肺炎克雷伯菌和金黄色葡萄球菌的最低抑菌浓度分别为125和250μg/ mL 。还对化合物7c进行了分子对接研究。
更新日期：2020-01-22
中文翻译：
结合分子对接研究一些新型的N5磺化和N1烷基化的吡唑衍生物及其抗菌活性
通过5-氨基-1 H-吡唑衍生物1与芳基磺酰氯的磺酰化反应合成了一些新颖的N 5-磺酰化4。另一方面，通过在不同条件下分别用氯乙酰胺和氯乙酸乙酯将化合物1烷基化，可以合成N 1-烷基化的吡唑7和10。化合物4和7与不同的芳族醛的缩合提供了相应的亚芳基衍生物。尽管如此，将10与芳族醛缩合仍可得到2-（5-氨基-2-芳基-1 H-吡唑-1-基）乙酸。通过元素分析和光谱数据阐明了新合成化合物的结构。此外，研究了其形成的建议机制。此外，针对抗微生物活性筛选了一些选定的新化合物。与标准抗生素制霉菌素（Nystatin）（IZD = 21±0.5 mm）相比，化合物7c对白色念珠菌具有更高的活性（抑制区直径[IZD] = 31.3±0.6 mm）。此外，化合物7c对肺炎克雷伯菌和金黄色葡萄球菌的最低抑菌浓度分别为125和250μg/ mL 。还对化合物7c进行了分子对接研究。
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