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目的研究含功能基侧链多(硫/氧)醚吡啶均三唑席夫碱衍生物的合成方法及抗癌活性。方法吡啶噻二唑硫醇(1)与甲氧乙氧氯甲烷进行亲核取代反应得多(硫/氧)醚吡啶噻二唑(2),与水合肼通过开-闭环加成-消除反应得中间体化合物多(硫/氧)醚吡啶均三唑(3),再与各种芳香醛缩合得相应席夫碱目标化合物。采用MTT法研究了目标化合物体外抑制L1210和B16癌细胞的活性。结果合成了12个新化合物,其结构经元素分析、IR、1H-NMR、MS确证。天然芳香醛席夫碱化合物4a,4b,4c,4d,4e表现明显的体外抗癌活性。结论天然芳香醛缩多(硫/氧)醚吡啶均三唑席夫碱衍生物有可能成为新型结构的抗癌先导化合物。
AIM: To study the synthesis and antitumor activity of Schiff base derivatives containing functional groups of side-chain poly (sulfur / oxygen) ether pyridines. Methods Pyridine thiadiazolethiol (1) was reacted with methoxyethoxychloride to nucleophilic substitution reaction (thiooxygen) ether pyridine pyridinethiadiazole (2), hydrazine hydrate through open-closed-loop addition-elimination reaction Intermediates compound (sulfur / oxygen) ether pyridine triazole (3), and then with a variety of aromatic aldehydes condensation of the corresponding Schiff base target compounds. The target compounds were used to inhibit the activity of L1210 and B16 cancer cells in vitro by MTT assay. Results Twelve novel compounds were synthesized and their structures were confirmed by elemental analysis, IR, 1H-NMR and MS. Natural aromatic aldehyde Schiff base compounds 4a, 4b, 4c, 4d, 4e showed significant anticancer activity in vitro. Conclusions Natural aromatic aldehyde condensation (sulfur / oxygen) ether pyridine triazine Schiff base derivatives may become a new type of anti-cancer lead compounds.