| 陈明秀,程莎,代兴,孟雪玲,徐广灿,徐必学.化学通报,2023,86(5):598-606,597. |
| 2-芳基-4-三氟甲基喹唑啉衍生物的合成及抗肿瘤活性研究 |
| Synthesis and Antitumor Activity of 2-Aryl-4-Trifluoromethylquinazoline Derivatives |
| 投稿时间：2022-10-13 修订日期：2022-11-15 |
| DOI： |
| 中文关键词: 喹唑啉 三氟甲基 抗肿瘤活性 MTT法 |
| 英文关键词:quinazoline trifluoromethyl antitumor activity MTT assays |
| 基金项目:贵州省高层次创新型人才培养计划项目(黔科合平台人才[2016]5678)和贵州省科技计划项目(黔科合基础-ZK[2021]一般070)资助 |
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| 中文摘要: |
| 为寻找高效低毒的含三氟甲基取代的喹唑啉类新型抗肿瘤活性化合物，以2-硝基-5-氯苯甲酸为原料，通过水解、还原、偶联、环合、三氟甲基加成消除等反应，设计合成了14个2-芳基-4-三氟甲基喹唑啉衍生物，并通过1H NMR、13C NMR、19F NMR等进行了结构确证。采用MTT法评价了目标化合物对PC3（前列腺癌细胞）、LNCaP（前列腺癌细胞）、K562（人慢性髓系白血病细胞）、HeLa（宫颈癌细胞）和A549（人肺癌细胞）等肿瘤细胞株的生长抑制活性。结果显示，在5 μmol·L-1浓度下，部分目标化合物对上述5种肿瘤细胞均具有较好的生长抑制活性，其中，化合物8c、13e对LNCaP细胞的IC50（半数抑制浓度）分别为2.9 μmol·L-1和1.9 μmol·L-1。通过本文的研究，建立了一种2-芳基-4-三氟甲基喹唑啉衍生物的快速合成方法，部分化合物对肿瘤细胞的生长具有较好的抑制作用，可为该类化合物的深入研究提供参考。 |
| 英文摘要: |
| To find anti-tumor quinazoline compounds with high efficiency and low toxicity, a series of novel 2-aryl-4-trifluoromethylquinazoline derivatives were synthesized starting from 5-chloro-2-nitrobenzoic acid by hydrolysis, reduction, coupling, cyclization, trifluoromethyl addition, and elimination reactions. The structures of target compounds were characterized by 1H NMR, 13C NMR and19F NMR. Their antitumor activities in vitro against five human cancer cell lines (PC3, LNCaP, K562, HeLa and A549) were demonstrated by MTT assay. The results indicated that some target compounds show inhibitory effect on five human cancer cell lines at 5 μmol·L-1. Among them, compounds 8c and 13e showed better activities against LNCaP antiproliferative with IC50 values of 2.9 μmol·L-1 and 1.9 μmol·L-1, respectively. In this study, a rapid synthesis method for the preparation of novel 2-aryl-4-trifluoromethylquinazoline derivatives has been developed, and some of these compounds exhibited certain inhibitory activity. The results of this study will provide a basis for further research on the derivatives of 2-aryl-4-trifluoromethylquinazoline. |
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