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宁虎林, 郭易华, 李凤凤, 李荣东.2-苯氨基喹啉衍生物的设计、合成及其抗肿瘤活性研究[J].湖南中医药大学学报英文版,2024,44(5):802-810.[Click to copy
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| 2-苯氨基喹啉衍生物的设计、合成及其抗肿瘤活性研究 |
| 宁虎林,郭易华,李凤凤,李荣东 |
| (湖南中医药大学, 湖南 长沙 410208;湖南九典制药股份有限公司, 湖南 长沙 410000) |
| 摘要: |
| 目的 在喹啉环的C-2位引入亲脂性苯胺基团，C-7位引入亲水性基团，得到新型2-苯氨基喹啉衍生物，探究其抗肿瘤细胞增殖活性。方法 以DL-苯丙氨酸、L-苯丙氨酸和D-苯丙氨酸为原料合成关键中间体，与喹啉母核连接合成一系列2-苯氨基喹啉衍生物。采用CCK-8法测试目标化合物对人肝癌细胞（HepG2）和非小细胞肺癌细胞（A549）的抗增殖活性。通过Autodock软件测试目标化合物与血管内皮生长因子受体（vascular endothelial growth factor receptor，VEGFR）、表皮生长因子受体（epidermal growth factor，EGFR）蛋白的结合效果。结果 合成了16个新型2-苯氨基喹啉衍生物，经1H NMR、LC-MS 确证其结构。体外抗肿瘤实验结果表明，目标化合物 T-7与T-8的抗肿瘤活性与阳性对照药吉非替尼以及乐伐替尼相当。Autodock软件预测结果与体外抗肿瘤实验结果一致。结论 新型2-苯氨基喹啉衍生物具有抗肝癌和非小细胞肺癌的作用，为进一步探究喹啉衍生物类抗肿瘤药物打下基础。 |
| 关键词: 2-苯氨基喹啉 肝癌 肺癌 细胞增殖 化学合成 |
| DOI：10.3969/j.issn.1674－070X.2024.05.012 |
| Received:November 07, 2023 |
| 基金项目:湖南中医药大学药学一流学科开放基金重点项目（2021YX01）。 |
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| Design, synthesis, and antitumor activity of 2-anilinoquinoline derivatives |
| NING Hulin, GUO Yihua, LI Fengfeng, LI Rongdong |
| (Hunan University of Chinese Medicine, Changsha, Hunan 410208, China;Hunan Jiudian Pharmaceutical Co., Ltd., Changsha, Hunan 410000, China) |
| Abstract: |
| Objective To yield a novel 2-anilinoquinoline derivative by introducing a lipophilic aniline group at the C-2 position of the quinoline ring and a hydrophilic group at the C-7 position, and to explore its anti-tumor cell proliferation activity. Methods Key intermediates were synthesized from DL-phenylalanine, L-phenylalanine, and D-phenylalanine, and a series of 2-anilinoquinoline derivatives were synthesized by linking them with quinoline nuclei. The anti-proliferative activity of the target compound on human liver cancer cells (HepgG2) and non-small cell lung cancer cells (A549) was tested using the CCK-8 method. The binding effects of the target compound with vascular endothelial growth factor receptor (VEGFR) and epidermal growth factor receptor (EGFR) proteins were determined by Autodock software. Results Sixteen new 2-anilinoquinoline derivatives were synthesized, and their structures were confirmed by 1H NMR and LC-MS. The results of in vitro anti-tumor experiments showed that the anti-tumor activities of target compounds T-7 and T-8 were comparable to those of the positive control medicines, Gefitinib and Lenvatinib. The test results of Autodock software were consistent with the results of in vitro anti-tumor experiments. Conclusion The novel 2-anilinoquinoline derivatives have effects against liver cancer and non-small cell lung cancer, laying a theoretical foundation for further exploration of quinoline derivatives as anti-tumor agents. |
| Key words: 2-anilinoquinolines liver cancer lung cancer cell proliferation chemical synthesis |
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