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香豆素衍生物的化学感觉特性：具有多种药理学特性的有前途的试剂，对接和 DFT 研究。

Chemosensing Properties of Coumarin Derivatives: Promising Agents with Diverse Pharmacological Properties, Docking and DFT Investigation.

机构信息

Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia.

Department of Chemistry, College of Science, Sana'a University, Sana'a P.O. Box 1247, Yemen.

出版信息

Molecules. 2022 Sep 12;27(18):5921. doi: 10.3390/molecules27185921.

DOI:10.3390/molecules27185921
PMID:36144656
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9503222/
Abstract

In this work, a three-component reaction of 3-acetyl-4-hydroxycoumarine, malononitrile, or cyanoacetate in the presence of ammonium acetate was used to form coumarin derivatives. The chemical structures of new compounds were identified by H, C NMR and an elemental analysis. These compounds were examined in vitro for their antimicrobial activity against a panel of bacterial strains. In addition, these compounds were investigated for antioxidant activities by superoxideradical, DPPH (2,2-Diphenyl-1-picrylhydrazyl), and hydroxyl radical scavenging assays, in which most of them displayed significant antioxidant activities. Furthermore, these compounds were evaluated for anti-inflammatory activity by indirect hemolytic and lipoxygenase inhibition assays and revealed good activity. In addition, screening of the selected compounds - against colon carcinoma cell lines (HCT-116) and hepatocellular carcinoma cell lines (HepG-2) showed that that 2-amino-4-hydroxy-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)nicotinonitrile exhibited good cytotoxic activity against standard Vinblastine, while the other compounds exhibited moderate cytotoxic activity. Docking simulation showed that2-amino-4-hydroxy-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)nicotinonitrile is an effective inhibitor of the tumor protein HCT-116. A large fluorescence enhancement in a highly acidic medium was observed, and large fluorescence quenching by the addition of traces of Cu and Ni was also remarked.

摘要

在这项工作中，使用 3-乙酰基-4-羟基香豆素、丙二腈或氰乙酸酯与醋酸铵一起进行了三组分反应，形成了香豆素衍生物。通过 H、C NMR 和元素分析确定了新化合物的化学结构。这些化合物在体外进行了抗菌活性测试，针对一系列细菌菌株进行了测试。此外，这些化合物还通过超氧自由基、DPPH（2,2-二苯基-1-苦基肼基）和羟基自由基清除测定法进行了抗氧化活性研究，其中大多数化合物表现出显著的抗氧化活性。此外，这些化合物还通过间接溶血和脂氧合酶抑制测定法进行了抗炎活性评估，显示出良好的活性。此外，对选定化合物 - 对结肠癌细胞系 (HCT-116) 和肝癌细胞系 (HepG-2) 的筛选表明，2-氨基-4-羟基-6-(4-羟基-2-氧代-2H-色烯-3-基)烟酰胺腈对标准长春新碱表现出良好的细胞毒性活性，而其他化合物则表现出中等的细胞毒性活性。对接模拟表明，2-氨基-4-羟基-6-(4-羟基-2-氧代-2H-色烯-3-基)烟酰胺腈是肿瘤蛋白 HCT-116 的有效抑制剂。在高度酸性介质中观察到大的荧光增强，并且通过添加痕量的 Cu 和 Ni 也观察到大的荧光猝灭。

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