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以1-甲基-β-咔啉为原料,经过硝化、N9-烷基化反应和还原胺化反应等步骤,合成了一系列新型的5-氯-β-咔啉衍生物,目标化合物的结构经1H NMR,13C NMR以及HRMS确证,并利用单晶X射线衍射分析了N-(吡啶-3-基)甲基-5-氯-1,9-二甲基-β-咔啉-6-胺(5e)的精确结构.采用噻唑蓝(MTT)法测试了目标化合物对肺癌细胞A549、胃癌细胞BGC-823、结肠癌细胞CT-26、肝癌细胞Bel-7402和乳腺癌细胞MCF-7的细胞增殖抑制作用.实验结果表明,部分化合物具有较好的抗肿瘤活性,其中N-(2,6-二氟苄基)-1-甲基-5-氯-9-(2,3,4,5,6-五氟苄基)-β-咔啉-6-胺(5j)和N-(吡啶-3-基甲基)-1-甲基-5-氯-9-(2,3,4,5,6-五氟苄基)-β-咔啉-6-胺(5m)对所测试的4种肿瘤细胞株均有较高的抑制活性,IC50值均小于10 μmol?L-1.“,”Sixteen novel 5-chloro-β-carboline derivatives were synthesized from harmane in four steps:N9-alkylation,nitra-tion,reduction,and Borch reduction.The structures of target compounds were confirmed by 1H NMR,13C NMR,and HRMS.A single crystal of 5-chloro-l,9-dimethyl-N-(pyridin-3-ylmethyl)-β-carboline(5e)was cultured,and its single crystal structure was determined by X-ray diffraction study.The in vitro antiproliferative activities were evaluated in a panel of cancer cell lines(A549,BGC-823,CT-26,Bel-7402,and MCF-7)via methyl thiazolyl tetrazolium(MTT)assay.The results indicated that some compounds had good activities,and especially N-(2,6-difluorobenzyl)-l-methyl-5-chloro-9-(2,3,4,5,6-pentafluorobenzyl)-β-carboline-6-amine(5j)and N-(pyridin-3-ylmethyl)-l-methyl-5-chloro-9-(2,3,4,5,6-pentafluorobenzyl)-β-carboline-6-amine(5m)showed considerable antitumor activity with IC50 values lower than 10 μmol?L-1 against four cancer cell lines.