Environmentally friendly synthesis and computational studies of novel class of acridinedione integrated spirothiopyrrolizidines/indolizidines

IF 3.8 4区 工程技术 Q2 CHEMISTRY, MULTIDISCIPLINARY
R. Raju, R. Raghunathan, N. Arumugam, A. Almansour, Raju Suresh Kumar, P. Vivekanand, C. Ebenezer, R. V. Solomon, Karthikeyan Perumal
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引用次数: 0

Abstract

Abstract An efficient and environmentally benign synthesis of a new class of acridinedione embedded spirooxindolo/acenaphthenothiopyrrolizidines and spirooxindolo/acenathenoindolizidines has been synthesized in good to excellent yields employing ionic liquid accelerated one-pot [3 + 2]-cycloaddition strategy. The pre-requisite starting substrates, O-acryloyl acridinediones were prepared from dimedone in three good yielding steps, while the 1,3-dipole was derived in situ from isatin/acenaphthenequinone and thiazolidine-4-carboxylc acid/l-pipecolinic acid via decarboxylative condensation. The cycloadduct possesses three stereogenic carbons, one of which is a spiro carbon through the formation of two C–C and one C–N bonds in one-pot synthetic transformation. Geometrical parameters of the synthesized compounds were calculated using the B3LYP/6-311g(d,p) level of theory. The activity of these molecules was evaluated against main protease of COVID-19 to screen them for their inhibitor efficiency. In order to get a broad understanding of the interactions of these synthesized ligands, a detailed molecular docking analysis was performed. Molecular docking analysis shows that compound 8b has the highest binding affinity toward the protein. The compound can be a potential candidate for the treatment of COVID-19.
新型吖啶二酮-螺硫基吡咯烷/中氮茚类化合物的环保合成及计算研究
摘要采用离子液体加速一锅[3+2]-环加成策略,以良好至优异的产率合成了一类新的吖啶二酮包埋螺氧吲哚/并噻吩并吡咯嗪和螺氧吲哚和并噻吩并氮茚二酮。先决条件的起始底物O-丙烯酰基吖啶二酮是由二酮通过三个高产步骤制备的,而1,3-偶极是由靛红/苊醌和噻唑烷-4-羧酸/l-哌啶酸通过脱羧缩合原位衍生的。环加合物具有三个立体碳,其中一个是螺碳,通过一锅合成转化形成两个C–C和一个C–N键。用B3LYP/6-311g(d,p)理论计算了合成化合物的几何参数。评估这些分子对新冠肺炎主要蛋白酶的活性,以筛选它们的抑制剂效率。为了广泛了解这些合成配体的相互作用,进行了详细的分子对接分析。分子对接分析表明,化合物8b对蛋白质具有最高的结合亲和力。该化合物可能是治疗新冠肺炎的潜在候选药物。
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来源期刊
Green Processing and Synthesis
Green Processing and Synthesis CHEMISTRY, MULTIDISCIPLINARY-ENGINEERING, CHEMICAL
CiteScore
6.70
自引率
9.30%
发文量
78
审稿时长
7 weeks
期刊介绍: Green Processing and Synthesis is a bimonthly, peer-reviewed journal that provides up-to-date research both on fundamental as well as applied aspects of innovative green process development and chemical synthesis, giving an appropriate share to industrial views. The contributions are cutting edge, high-impact, authoritative, and provide both pros and cons of potential technologies. Green Processing and Synthesis provides a platform for scientists and engineers, especially chemists and chemical engineers, but is also open for interdisciplinary research from other areas such as physics, materials science, or catalysis.
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