2-(取代氨基)-N-(6-取代-1,3-苯并噻唑-2-基)乙酰胺的合成、分子对接和抗菌评价。

Smita Pawar, Amol Kale, Priya Zori, Dhanashri Zope
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引用次数: 0

摘要

背景:出于多种原因,开发抗菌剂至关重要,主要是为了防治传染病和应对日益严重的抗菌剂耐药性威胁。尽管存在许多现有药物,但由于新病原体和疾病的出现、对现有药物的抗药性以及对现有药物的多重抗药性的传播等原因,抗菌药物的持续开发仍有必要:本研究旨在合成和评估新合成的苯并噻唑衍生物的抗菌潜力:方法:通过氯乙酰氯与取代的 2-氨基苯并噻唑反应,合成了一系列新的 2-(取代氨基)-N-(6-取代-1,3-苯并噻唑-2 基)乙酰胺 BTC(a-t),并与各种取代胺进一步回流得到目标化合物。实验筛选了合成化合物对革兰氏阳性和阴性细菌及真菌的抗菌特性。对选定的细菌和真菌菌株测定了化合物的抑菌区和最低抑菌浓度。使用 V-life MDS 3.5 软件(DNA gyrase,PDB:3G75)进行了进一步的对接研究,以检查与所选蛋白质的可能相互作用:发现化合物 BTC-j N-(6-甲氧基-1,3-苯并噻唑-2-基)-2-(吡啶-3-基氨基)乙酰胺和 BTC-r N-(6-硝基-1,3-苯并噻唑-2-基)-2-(吡啶-3-基氨基)乙酰胺具有良好的抗菌潜力。化合物 BTC-j 对金黄色葡萄球菌(MIC 值为 12.5 μg/mL)、枯草杆菌(MIC 值为 6.25 μg/mL)、大肠杆菌(MIC 值为 3.125 μg/mL)和绿脓杆菌(MIC 值为 6.25 μg/mL)具有良好的抗菌活性。因此,从结果中可以看出,化合物 BTC-j、BTC-f、BTC-n 和 BTC-r 在不同浓度下具有显著的抗菌和抗真菌潜力:本研究成功合成了 2-乙酰氨基取代的苯并噻唑衍生物 BTC(a-t),产率良好。化合物的 dock 评分和抗菌活性一致。标准化合物和受试化合物的抗菌活性没有统计学差异,表明受试化合物具有相当的活性。因此,苯并噻唑与具有乙酰胺连接的杂环连接,可作为有希望的先导分子,在发现强效抗菌剂的过程中进一步优化。因此,我们得出结论:合成的化合物具有作为新型抗菌剂进一步开发的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis, Molecular Docking, and Antimicrobial Evaluation of 2-(Substituted Amino)-N-(6-Substituted-1,3-Benzothiazol-2yl) Acetamide.

Background: The development of antimicrobial agents is crucial for several reasons, primarily to combat infectious diseases and to address the growing threat of antimicrobial resistance. The need for the contin-ued development of antimicrobial drugs persists despite the presence of many existing drugs for several reasons viz; emerging new pathogens and diseases, reistance to existing drug and propogation of multi-drug resistance to existing drugs.

Objective: The objective of the study was to synthesize and evaluate the antimicrobial potential of newly synthesized benzothiazole derivatives.

Methods: A new series of 2-(substituted amino)-N-(6-substituted-1,3-benzothiazol-2yl)acetamide BTC(a-t) has been synthesized by reacting it with chloracetyl chloride with substituted 2-amino benzothiazole and further refluxed with various substituted amines to obtain target compounds. The synthesized compounds were screened experimentally for their antimicrobial property against gram-positive and gram-negative bacteria and fungi. The zone of inhibition and minimum inhibitory concentration of compounds were determined against selected bacterial and fungal strains. Further docking study was carried out to check the probable interactions with the selected protein using V-life MDS 3.5 software (DNA gyrase, PDB: 3G75).

Result: Compounds BTC-j N-(6-methoxy-1,3-benzothiazol-2-yl)-2-(pyridine-3-ylamino)acetamide and BTC-r N-(6-nitro-1,3-benzothiazol-2-yl)-2-(pyridine-3-ylamino)acetamide were found to have good antimicrobial potential. The compound BTC-j showed good antibacterial activity against S. aureus at an MIC value of 12.5 μg/mL, B. subtilis at MIC of 6.25μg/mL, E. coli at MIC of 3.125μg/mL, and P. aeruginosa at MIC of 6.25μg/mL. Thus, from the result, it was observed that compounds BTC-j, BTC-f, BTC-n, and BTC-r exhibited significant antibacterial and antifungal potential at different concentrations.

Conclusion: The present study resulted in the successful synthesis of 2-acetamido substituted benzothiazole derivatives BTC(a-t) with good yields. The dock score of the compounds and the antimicrobial activity were found to be consistent. No statistical difference in the antimicrobial activity of the standard and test compounds was found, indicating that the test compounds have comparable activity. Therefore, benzothiazole linked to heterocyclic rings with an acetamide linkage may serve as promising lead molecules for further optimization in the journey to discover potent antibacterial agents. Thus, we conclude that the synthesized compounds have the potential for further development as novel antimicrobial agents.

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