Green synthesis, anti-inflammatory evaluation and molecular docking of novel pyridines via one pot multi-component reaction using ultrasonic irradiation.

IF 3.9 2区 化学 Q2 CHEMISTRY, APPLIED Molecular Diversity Pub Date : 2024-12-07 DOI:10.1007/s11030-024-11073-7
Nadia A A Elkanzi, Ali M Ali, Mahmoud A Abdelaziz, Alaa Muqbil Alsirhani
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Abstract

In this paper, we present a green application for the synthesis of novel pyridine derivatives 4a-f via one-pot, multicomponent reaction (MCRs) of some aromatic aldehydes 1a-f with malononitrile (2) and N-(4-acetylphenyl)-4-methylbenzenesulfonamide (3) in the presence of ammonium acetate using ultrasonic irradiation (U.S) in an aqueous solvent H2O:EtOH (2:1). The structures of all synthesized pyridines 4a-f were confirmed via elemental analysis and different spectroscopic techniques. This application has many advantages such as avoiding hazardous solvents, excellent yields, inexpensive, simple application, in addition to obtain pure compounds. The anti-inflammatory activity of the newly compounds was examined with the reference drug Ibuprofen. The obtained results showed that most derivatives are promising anti-inflammatory activates. Moreover, compound 4b exhibits the most anti-inflammatory activity with a percentage of inhibition with 51.67% compared with Ibuprofen 53.96%. Furthermore, the newly compounds were studied in their molecular docking simulations against the enzyme Human Cyclooxygenase-2, with Tolfenamic Acid as a reference ligand (PDB ID: 5IKT). Compound 4b demonstrated a robust binding affinity with the target protein 5ikt, evidenced by its binding affinity score of - 11.16 kcal/mol, which is the highest among the studied compounds.

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超声辐照一锅多组分反应绿色合成、抗炎评价及分子对接。
本文介绍了一种新型吡啶衍生物4a-f的绿色合成方法,即在乙酸铵存在下,利用超声辐照(us)在水:乙氧乙酸(2:1)的水溶液中,通过与丙二腈(2)和N-(4-乙酰苯基)-4-甲基苯磺酰胺(3)的一锅多组分反应(mcr)合成新型吡啶衍生物4a-f。通过元素分析和不同的光谱技术确定了所有合成的4a-f吡啶的结构。该应用具有避免使用有害溶剂、收率优异、价格低廉、应用简单、除可获得纯化合物等优点。新化合物的抗炎活性与对照药物布洛芬进行了比较。结果表明,大多数衍生物具有良好的抗炎活性。此外,化合物4b的抗炎活性最高,抑制率为51.67%,而布洛芬的抑制率为53.96%。此外,以甲苯胺酸为参考配体(PDB ID: 5IKT),研究了新化合物与Human cycloxygenase -2的分子对接模拟。化合物4b与靶蛋白5ikt具有较强的结合亲和力,其结合亲和力评分为- 11.16 kcal/mol,是所研究化合物中最高的。
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来源期刊
Molecular Diversity
Molecular Diversity 化学-化学综合
CiteScore
7.30
自引率
7.90%
发文量
219
审稿时长
2.7 months
期刊介绍: Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;
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