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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。
AIM: To synthesize 2- (quinoxalinyl) -2- (benzotriazolyl) acetonitrile and its derivatives and test its inhibitory effects on the proliferation of SGC-7901 and Hep G2 tumor cells. Methods: 2,3-Dichloroquinoxaline and 2- (2H-benzo [d] [1,2,3] triazol-2-yl) 2-yl) -2- (2H- benzo [d] [1,2,3] triazol-2-yl) acetonitrile and its derivatives (1a ~ 3c) The resulting product was tested for antitumor activity. Results: Nine corresponding target compounds were synthesized and the structures were confirmed by IR and 1H NMR. The target substance has better inhibitory effect on human gastric cancer SGC-7901 cells than human hepatoma Hep G2 cells, wherein the compound 2- (3,7-dichloroquinoxalin-2-yl) -2- 1,2,3] triazol-2-yl) acetonitrile compounds (3a ~ 3c) on human gastric cancer SGC-7901 cells were stronger inhibitory effect, quinoxaline unit product (1b) and 6-chloroquinoxaline unit The IC50 value of product (3a) on SGC-7901 cell proliferation was 5.05 and 5.38 μg · mL -1, respectively. Conclusion: The introduction of chlorine atom at the 5-position of benzotriazole ring into methyl or quinoxaline ring can increase its biological activity. The target compounds (1b, 3a) can be structurally optimized to improve their anti-tumor activity.