| 文峻,张辉兰,陈诚,朱珠,李光耀,黄鹏,栗进才.化学通报,2025,88(1):109-115. |
| NO供体型紫檀芪查尔酮类衍生物的合成及抗肿瘤活性研究 |
| Synthesis and anti-tumour activity of NO donor-type Pterostilbene chalcone derivatives |
| 投稿时间：2024-08-09 修订日期：2024-09-19 |
| DOI： |
| 中文关键词: 紫檀芪 查尔酮 丹皮酚 合成 抗肿瘤活性 |
| 英文关键词:pterostilbene chalcone salvia divinorum synthesis antitumour activity |
| 基金项目:安徽省高校自然科学研究项目(KJ2020A0422)和安徽省高校协同创新项目(GXXT-2023-073)资助 |
|
| 摘要点击次数: 214 |
| 全文下载次数: 63 |
| 中文摘要: |
| 以紫檀芪为先导化合物，引入醛基，并与丹皮酚通过Claisen-Schmidt缩合反应得到紫檀芪丹皮酚查尔酮，再与不同碳链长度的二溴烷烃反应后，得到相应的紫檀芪溴代中间体，最终与硝酸银反应，得到5个紫檀芪查尔酮硝酸酯类衍生物。所有目标化合物结构经1H NMR、HRMS、13C NMR确证。采用CCK-8法评价目标化合物对人肝癌细胞HepG2和人非小细胞肺癌细胞A549的体外抗肿瘤活性，同时采用Griess法检测目标化合物4b、4e对HepG2细胞中NO释放的影响。实验结果表明，所有化合物的抑制活性均优于先导化合物紫檀芪，其中化合物4e对HepG2细胞有显著的抑制活性，IC50值为32 μM；化合物4b对A549细胞有较强的抑制活性，IC50值为7.86 μM；且化合物4b、4e在细胞中能释放高浓度的NO，分子对接结果显示它们与一氧化氮合酶靶蛋白具有较好的结合能，其发挥抗肿瘤作用可能与NO释放相关。 |
| 英文摘要: |
| Pterostilbene was used as the lead compound, the aldehyde group was introduced and reacted with salvinorin via Claisen-Schmidt condensation to obtain pterostilbene salvinorin chalcone, and then responded with dibromo alkanes of different carbon chain lengths to obtain the corresponding pterostilbene bromo intermediates, and finally reacted with silver nitrate to obtain five pterostilbene chalcone nitrate derivatives. The structures of all the target compounds were confirmed by 1H NMR, HRMS, and 13C NMR. The in vitro antitumor activities of the target compounds against human hepatocellular carcinoma cells HepG2 and human non-small cell lung cancer cells A549 were evaluated using the CCK-8 method. In contrast, the effects of the target compounds 4b and 4e on the release of NO from HepG2 cells were detected using the Griess method. The experimental results showed that the inhibitory activities of all the compounds were better than the lead compound pterostilbene, among which compound 4e had significant inhibitory activity on HepG2 cells with an IC50 value of 32 μM; compound 4b had strong inhibitory activity on A549 cells with an IC50 value of 7.86 μM; and compounds 4b and 4e could release high concentration of NO in the cells, and the results of molecular docking showed that The molecular docking results showed that they had better binding energy with nitric oxide synthase target protein, and their antitumor effects might be related to NO release. |
| 查看全文 查看/发表评论 下载PDF阅读器 |
| 关闭 |