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目的设计合成一系列4-胺甲酰-1,5-双芳基-1,2,3-三氮唑类化合物,并评价其抗肿瘤活性。方法以叠氮化钠为原料,经亲核取代反应制成有机叠氮化物后与丙炔酸甲酯通过Huisgen 1,3-偶极环加成反应得到5-碘代-1,2,3-三氮唑,再与单质硫和苄溴类化合物经3步连续反应“一锅法”得到1-对甲氧基苄基-4-甲氧甲酰-5-苄基硫醚-1,2,3-三氮唑,对三氮唑环上的4-甲氧甲酰基进行胺解反应得到目标化合物。采用MTT法测定目标化合物对人乳腺癌细胞(MCF-7)、肝癌细胞(Hep G2)、肺癌细胞(A549)和宫颈癌细胞(He La)的抑制活性。结果与结论合成了15个未见报道的4-胺甲酰-1,5-双芳基-1,2,3-三氮唑类化合物,其结构经1H-NMR、13C-NMR及HR-MS谱确证。其中,化合物7a对Hep G2、A549和He La细胞均表现出中等程度的抑制活性(IC50值分别为23.00、33.88、26.66μmol·L-1),有进一步研究的价值。
Aim To design and synthesize a series of 4-carbamoyl-1,5-bisaryl-1,2,3-triazole compounds and evaluate their anti-tumor activity. Methods Sodium azide was used as a starting material to prepare organic azides by nucleophilic substitution reaction. Methyl propionate was subjected to 1,3-dipolar cycloaddition with Huisgen to give 5-iodo-1,2,3 - triazole, and then with the elemental sulfur and benzyl bromide by 3-step continuous reaction “one-pot method ” 1-p-methoxybenzyl-4-methoxy-5-benzyl sulfide - 1,2,3-triazole, the trimethoxazole ring 4-methoxy-formyl amine to obtain the target compound. The inhibitory activities of the target compounds on human breast cancer cells (MCF-7), Hep G2, A549 and He La cells were determined by MTT assay. RESULTS AND CONCLUSION Fifteen novel 4-carbamoyl-1,5-bisaryl-1,2,3-triazoles were synthesized and their structures were confirmed by 1H-NMR, 13C-NMR and HR- MS spectral confirmation. Among them, compound 7a showed moderate inhibitory activity on Hep G2, A549 and He La cells (IC50 values were 23.00,33.88,26.66μmol·L-1, respectively), which has the value of further research.