O-Allyloxy chalcone derivatives: design, synthesis, anticancer activity, network pharmacology and molecular docking

IF 2.2 4区化学 Q2 Engineering

Chemical Papers Pub Date : 2024-10-09 DOI:10.1007/s11696-024-03723-9

Shweta Umar, Sudhir Katariya, Rina Soni, Shubhangi S. Soman, B. Suresh

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引用次数: 0

Abstract

A series of (2E)-3-[2,4-bis(2-propen-1-yloxy)phenyl]-1-phenyl]-2-propen-1-ones—chalcone derivatives with O-allyloxy groups—were synthesized in good yields and characterized by different analytical techniques. Their anticancer activity was evaluated against the A549 (lung cancer) cell line. The most active compounds of this series were the 1-(4-fluorophenyl derivative 9c (IC₅₀ = 0.48 ± 0.07 µM) and the 1-(4-octyloxy)phenyl derivative 9f (IC₅₀ = 0.04 ± 0.01 µM). Network pharmacology analysis using the SwissTarget and DisGeNet databases identified potential targets for 9c in the Non-Small Cell Lung Carcinoma (NSCLC) cell line. Protein–Protein Interaction (PPI) network analysis revealed seven hub genes: MAPK14, PTGS2, HSP90AA1, MAPK8, NOS2, SYK, and NR3C1. Gene ontology analysis highlighted diverse biological functions. KEGG pathway analysis implicated pathways in cancer and immunoregulation. Molecular docking analysis suggested a strong interaction between 9c with MAPK14 (calculated docking score of –8.4 kcal mol^–1). Compound 9c's potent activity warrants further preclinical and clinical evaluation as a potential NSCLC therapy Based on this results, study of heterocyclic compounds with O-allyloxy groups will help to explore their impact on anticancer activity and mechanistic pathway.

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O-烯丙氧基查尔酮衍生物：设计、合成、抗癌活性、网络药理学和分子对接

我们合成了一系列(2E)-3-[2,4-双(2-丙烯-1-基氧基)苯基]-1-苯基]-2-丙烯-1-酮-带有 O-烯丙氧基基团的查耳酮衍生物，产量良好，并通过不同的分析技术对其进行了表征。评估了它们对 A549（肺癌）细胞系的抗癌活性。该系列中活性最强的化合物是 1-(4-氟苯基)衍生物 9c（IC50 = 0.48 ± 0.07 µM）和 1-(4-辛氧基)苯基衍生物 9f（IC50 = 0.04 ± 0.01 µM）。利用 SwissTarget 和 DisGeNet 数据库进行的网络药理学分析确定了 9c 在非小细胞肺癌 (NSCLC) 细胞系中的潜在靶点。蛋白质-蛋白质相互作用（PPI）网络分析发现了七个中心基因：基因本体分析强调了不同的生物功能。KEGG 通路分析显示了癌症和免疫调节的相关通路。分子对接分析表明，9c 与 MAPK14 之间有很强的相互作用（对接计算得分为 -8.4 kcal mol-1）。化合物 9c 的强效活性值得作为一种潜在的 NSCLC 治疗方法进行进一步的临床前和临床评估。

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来源期刊

Chemical Papers Chemical Engineering-General Chemical Engineering

CiteScore

3.30

自引率

4.50%

发文量

590

期刊介绍： Chemical Papers is a peer-reviewed, international journal devoted to basic and applied chemical research. It has a broad scope covering the chemical sciences, but favors interdisciplinary research and studies that bring chemistry together with other disciplines.