苯并三唑缀合喹喔啉类化合物的合成与抗肿瘤活性

发布时间：2018-01-14 06:34

本文关键词：苯并三唑缀合喹喔啉类化合物的合成与抗肿瘤活性　出处：《中国新药杂志》2017年13期 　论文类型：期刊论文

【摘要】：目的:合成2-(喹喔啉基)-2-(苯并三唑基)乙腈及其衍生物,并测试其对SGC-7901和Hep G2肿瘤细胞增殖的抑制作用。方法:2,3-二氯喹喔啉和2-(2H-苯并[d][1,2,3]三唑-2-基)乙腈及其衍生物通过亲核取代反应得到2-(3-氯喹喔啉-2-基)-2-(2H-苯并[d][1,2,3]三唑-2-基)乙腈类化合物及其衍生物(1a~3c),并用MTT法测试所得产物的抗肿瘤活性。结果:合成得到9个相应的目标化合物,通过IR和1H NMR确认结构。标的物对人胃癌SGC-7901细胞的抑制效果较人肝癌Hep G2细胞好,其中化合物2-(3,7-二氯喹喔啉-2-基)-2-(2H-苯并[d][1,2,3]三唑-2-基)乙腈类化合物(3a~3c)对人胃癌SGC-7901细胞的抑制效果都较强,喹喔啉单元产物(1b)和6-氯喹喔啉单元产物(3a)对SGC-7901细胞增殖抑制IC50值分别为5.05和5.38μg·mL~(-1)。结论:苯并三唑环5-位引入甲基或喹喔啉环6-位引入氯原子可以提高其生物活性,标的物(1b,3a)可以进行结构优化,以期提高其抗肿瘤活性。
[Abstract]:Objective: to synthesize 2-( quinoxalinyl) -2-( benzotriazolyl) acetonitrile and its derivatives, and to test their inhibitory effects on the proliferation of SGC-7901 and Hep G2 cells. 3-Dichloroquinoxaline and 2-O2H-Benzo. [D]. [The nucleophilic substitution reaction of acetonitrile and its derivatives resulted in the synthesis of 2-trichloroquinoxaline -2-oxaline-2-butadiene-2H-benzo by nucleophilic substitution reaction with triazole-2-yl) acetonitrile and its derivatives by nucleophilic substitution reaction. [D]. [The antineoplastic activity of the product was tested by MTT method. Results: nine corresponding target compounds were synthesized. The structure was confirmed by IR and 1H NMR. The inhibitory effect of the subject matter on human gastric cancer SGC-7901 cells was better than that on human hepatoma Hep G2 cells. 7- dichloroquinoxaline-2----. [D]. [The inhibitory effect of triazole-2-yl) acetonitrile compounds on human gastric cancer SGC-7901 cells was stronger. The inhibitory IC50 values of quinoxaline unit product and 6-chloroquine unit product on the proliferation of SGC-7901 cells were 5.05 and 5.38 渭 g 路mL ~ (-1), respectively. Conclusion: the addition of methyl or quinoxaline at 5-site of benzo-triazole ring can improve its biological activity. In order to improve its anti-tumor activity, the subject matter can be optimized for 3 years.
【作者单位】：福建医科大学药学院;
【基金】：福建省自然科学基金资助项目(2013J01375,2015J01316)
【分类号】：R914;R96
【正文快照】： 喹喔啉与苯并三唑是由苯环与含氮杂环拼合而成的杂环类化合物,前者氮杂环是吡嗪,后者是三唑。化学结构分析这两类化合物与碱基腺嘌呤和鸟嘌呤互为生物电子等排体。分子生物学和生物信息学研究表明,这些稠杂环芳香物质是构成生命物质基础蛋白质和核酸的重要成分,且在生物细胞的

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