结合光谱技术合成并表征了 8​​-芳基-、8-苯乙烯基-和 8-芳基乙炔基取代的 5-甲氧基黄酮。对代表性化合物 3h 的单晶 X 射线衍射 (XRD) 研究表明，反向二聚体由涉及分子间 CO⋯HC 和 CH⋯OC 氢键的稠合十元环和六元环基序连接。化合物 3b、3c、3d、4a 和 4b 对人乳腺癌 (MCF-7) 癌细胞系表现出很强的活性（IC50 分别 = 13.68 ± 0.72、16.91 ± 0.40、13.63 ± 0.36、14.66 ± 0.47 和 12.26 ± 0.45 μM） ）和肺癌（A549）癌细胞系（IC50 = 15.38 ± 0.33、10.00 ± 0.28、12.38 ± 0.30、12.84 ± 0.33 和 8.47 ± 0.30 μM，分别）与槲皮素（IC50 = 40.61 ± 1.07 和 58）相比.17±0.50μM，分别）。化合物3b、3c和4b对血管内皮生长因子受体2(VEGFR-2)和表皮生长因子受体(EGFR)酪氨酸激酶磷酸化表现出双重抑制作用。分子对接表明，与酶主链的强对齐主要是通过疏水性（π-π 和 π-H）接触以及通过与 VEGFR-2 和 EGFR 活性位点残基的氢键相互作用来实现的。测试化合物具有良好的药物相似性，支持其作为有前途的治疗候选者的潜力。版权所有 © 2024 作者。由爱思唯尔公司出版。保留所有权利。

The 8-aryl-, 8-styryl- and 8-arylethynyl substituted 5-methoxyflavones were synthesized and characterized using a combination of spectroscopic techniques. Single crystal X-ray diffraction (XRD) study on a representative compound 3h shows an inverted dimer linked by fused ten and six-membered ring motifs involving intermolecular CO⋯HC and CH⋯OC hydrogen bonds. Compounds 3b, 3c, 3d, 4a and 4b exhibited strong activity against the human breast (MCF-7) cancer cell line (IC50 = 13.68 ± 0.72, 16.91 ± 0.40, 13.63 ± 0.36, 14.66 ± 0.47 and 12.26 ± 0.45 μM, respectively) and lung (A549) cancer cell line (IC50 = 15.38 ± 0.33, 10.00 ± 0.28, 12.38 ± 0.30, 12.84 ± 0.33 and 8.47 ± 0.30 μM, respectively) compared to quercetin (IC50 = 40.61 ± 1.07 and 58.17 ± 0.50 μM, respectively). Compounds 3b, 3c and 4b exhibited dual inhibitory effect against the vascular endothelial growth factor receptor-2 (VEGFR-2) and the epidermal growth factor receptor (EGFR) tyrosine kinase phosphorylation. Molecular docking revealed that strong alignment with the enzyme backbone is achieved mostly by hydrophobic (π-π, and π-H) contacts and by hydrogen bonding interaction with the residues in the active sites of VEGFR-2 and EGFR. The test compounds possess favorable drug-likeness properties, supporting their potential as promising therapeutic candidates.Copyright © 2024 The Author(s). Published by Elsevier Inc. All rights reserved.