Synthesis, antimicrobial and antioxidant activity with in silico ADMET prediction, molecular docking and dynamics studies of carbazole ring containing thiazole Schiff bases

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-09-05 DOI:10.1002/ajoc.202400363

Sumita Saznin Marufa, Mohammad Mostafizur Rahman, Md. Mizanur Rahman, Rownok Jahan, Gulshan Ara, Hiroshi Nishino, Mohammad Sayed Alam, Md. Aminul Haque

{"title":"Synthesis, antimicrobial and antioxidant activity with in silico ADMET prediction, molecular docking and dynamics studies of carbazole ring containing thiazole Schiff bases","authors":"Sumita Saznin Marufa, Mohammad Mostafizur Rahman, Md. Mizanur Rahman, Rownok Jahan, Gulshan Ara, Hiroshi Nishino, Mohammad Sayed Alam, Md. Aminul Haque","doi":"10.1002/ajoc.202400363","DOIUrl":null,"url":null,"abstract":"Twelve thiazole hybrids (2a‐2l) were synthesized in this study incorporating with Schiff base and carbazole scaffolds and characterized by spectral analyses. Antimicrobial activity and antioxidant potency were investigated by agar disc diffusion method and DPPH free radical scavenging assays where trimethyldihydrothiazole 2c had revealed its higher efficacy in both biological studies. It had displayed IC50 of 25.55 ± 0.40 µg/mL which is higher than the standard ascorbic acid (IC50 = 41.31 ± 1.83 µg/mL) as well as dihydrothiazoylchromenone 2e showed promising antioxidant activity with IC50 value of 40.82 ± 0.54. The compound 2c satisfied all the ADME properties and toxicological parameters with maximum drug score value (0.39) among all derivatives. Molecular docking was undertaken for higher bioactive compounds where 2c revealed its wide range of interactions with different amino acid residues which was also endorsed with the output of molecular dynamics simulation.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ajoc.202400363","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

Abstract

Twelve thiazole hybrids (2a‐2l) were synthesized in this study incorporating with Schiff base and carbazole scaffolds and characterized by spectral analyses. Antimicrobial activity and antioxidant potency were investigated by agar disc diffusion method and DPPH free radical scavenging assays where trimethyldihydrothiazole 2c had revealed its higher efficacy in both biological studies. It had displayed IC50 of 25.55 ± 0.40 µg/mL which is higher than the standard ascorbic acid (IC50 = 41.31 ± 1.83 µg/mL) as well as dihydrothiazoylchromenone 2e showed promising antioxidant activity with IC50 value of 40.82 ± 0.54. The compound 2c satisfied all the ADME properties and toxicological parameters with maximum drug score value (0.39) among all derivatives. Molecular docking was undertaken for higher bioactive compounds where 2c revealed its wide range of interactions with different amino acid residues which was also endorsed with the output of molecular dynamics simulation.

查看原文本刊更多论文

含噻唑席夫碱的咔唑环的合成、抗菌和抗氧化活性，以及硅学 ADMET 预测、分子对接和动力学研究

本研究结合希夫碱和咔唑支架合成了 12 种噻唑杂化物（2a-2l），并通过光谱分析对其进行了表征。通过琼脂盘扩散法和 DPPH 自由基清除试验，研究了三甲基二氢噻唑 2c 的抗菌活性和抗氧化效力。它的 IC50 值为 25.55 ± 0.40 µg/mL，高于标准抗坏血酸（IC50 = 41.31 ± 1.83 µg/mL）；二氢噻唑基色原酮 2e 的 IC50 值为 40.82 ± 0.54，显示出良好的抗氧化活性。化合物 2c 符合所有 ADME 特性和毒理学参数，在所有衍生物中药物得分最高（0.39）。对生物活性较高的化合物进行了分子对接，结果表明 2c 与不同的氨基酸残基有广泛的相互作用，分子动力学模拟的结果也证实了这一点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.