Synthesis, Molecular Docking, Anti-cholinesterase Activity, Theoretical Investigation, and Catalytic Effect of New Encumbered N-benzyladamantyl Substituted Imidazolidin-2-ylidene Carbene Pd-PEPPSI Complexes

IF 1.7 3区 化学 Q3 CHEMISTRY, ORGANIC
Sofiane ikhlef, Sarra Lasmari, Saber Mustapha Zendaoui, El Hassen Mokrani, Dahmane Tebbani, Nevin Gürbüz, Chawki Bensouici, Raouf Boulcina, Bachir Zouchoune, Ismail Özdemir
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Abstract

: This study aimed to describe the preparation of novel PEPPSI type Pd(II)-NHC complexes bearing N-benzyladamantyl substituted imidazolidin-2-ylidene group. All synthesized compounds were characterized by using 1 H-NMR and 13C-NMR spectroscopies, FTIR, and elemental analysis techniques. One of the objectives of this study was the synthesis of Pd-NHC complexes with AChE/BChE inhibition activities. Among all the tested compounds, complexes 4b and 4c were found to have the most high potential AChE and BChE inhibitory activities with IC50 values of 21.57 ± 0.23 Mm and 15.78 ± 0.39 Mm, respectively. Conducting molecular docking studies helped us in gathering crucial information about the main binding interactions of inhibitors and enzymes, and the results were in agreement with the biological evaluation. The synthesized Pd-NHC complexes were employed for catalyzing the direct C2- and C5-arylation reaction between aryl (hetero) halide and a variety of heterocyclic systems. In both cases (C2 and C5-arylation), Pd-NHC complexes catalysts provided access to the arylated heterocycles in good to high yields in the presence of 1 mol% catalyst loading at 150 °C. The DFT theoretical investigation showed that the Pd-NHC complexes were of ML2X2 type, where the the Pd(II) cation had a square planar geometry. The interaction energies obtained by energy decomposition analysis (EDA) demonstrated that the 4d and 4e complexes were more stable in the presence of more methyl substituents. The chemical indicators demonstrated that the less stable 4c complex was more reactive in regard to the chemical hardness, chemical potential, and electrophilicity values.
N-苄基-2-咪唑烷基-2-亚基碳烯 Pd-PEPPSI 新包合物的合成、分子对接、抗胆碱酯酶活性、理论研究和催化作用
:本研究旨在描述新型 PEPPSI 型 Pd(II)-NHC 配合物的制备过程,这些配合物带有 N-苄基氨基甲酰基取代的咪唑烷-2-亚基。利用 1 H-NMR 和 13C-NMR 光谱、傅立叶变换红外光谱以及元素分析技术对所有合成化合物进行了表征。本研究的目标之一是合成具有 AChE/BChE 抑制活性的 Pd-NHC 复合物。在所有测试化合物中,发现复合物 4b 和 4c 具有最强的潜在 AChE 和 BChE 抑制活性,其 IC50 值分别为 21.57 ± 0.23 Mm 和 15.78 ± 0.39 Mm。分子对接研究有助于我们收集抑制剂与酶的主要结合相互作用的关键信息,其结果与生物学评价一致。合成的 Pd-NHC 复合物被用于催化芳基(杂)卤化物与多种杂环体系之间的直接 C2 和 C5 芳基化反应。在这两种情况下(C2 和 C5-芳基化),Pd-NHC 配合物催化剂在 150 °C、催化剂负载量为 1 mol%的条件下,都能以良好到较高的产率获得芳基化杂环。DFT 理论研究表明,Pd-NHC 复合物属于 ML2X2 类型,其中 Pd(II) 阳离子具有正方形平面几何结构。通过能量分解分析(EDA)获得的相互作用能表明,甲基取代基越多,4d 和 4e 复合物越稳定。化学指标表明,稳定性较差的 4c 复合物在化学硬度、化学势和亲电性值方面反应性更强。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Current Organic Chemistry
Current Organic Chemistry 化学-有机化学
CiteScore
3.70
自引率
7.70%
发文量
76
审稿时长
1 months
期刊介绍: Current Organic Chemistry aims to provide in-depth/mini reviews on the current progress in various fields related to organic chemistry including bioorganic chemistry, organo-metallic chemistry, asymmetric synthesis, heterocyclic chemistry, natural product chemistry, catalytic and green chemistry, suitable aspects of medicinal chemistry and polymer chemistry, as well as analytical methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by chosen experts who are internationally known for their eminent research contributions. The Journal also accepts high quality research papers focusing on hot topics, highlights and letters besides thematic issues in these fields. Current Organic Chemistry should prove to be of great interest to organic chemists in academia and industry, who wish to keep abreast with recent developments in key fields of organic chemistry.
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