1,3,4-噁二唑三氮烯衍生物的合成及生物活性测定
收稿日期: 2015-07-03
修回日期: 2015-10-07
网络出版日期: 2015-10-26
基金资助
国家自然科学基金(No. J1210060)、河南省科技攻关计划(No. 0624420031)、河南省基础研究基金(No. 022463001)资助项目
Synthesis and Biological Activities of 1,3,4-Oxadiazole Triazene Derivatives
Received date: 2015-07-03
Revised date: 2015-10-07
Online published: 2015-10-26
Supported by
Project supported by the National Natural Science Foundation of China (No. J1210060), the Science and Technology Planning Project of Henan Province (No. 0624420031) and the Basic Research Development Program of Henan Province (No. 022463001)
利用拼合原理, 将具有生物活性的三氮烯结构与1,3,4-噁二唑结构相拼合, 设计合成了11个未见报道的1,3,4-噁二唑三氮烯衍生物. 所合成化合物经1H NMR, IR和HRMS得到表征. 用四甲基偶氮唑盐(MTT)法法评价了该类化合物对胃癌细胞(MGC803)和前列腺癌细胞(PC-3)的抑制作用, 结果显示化合物2-[4-(3,3-二甲基三氮烯-1-基)苯基]-5-(4-甲氧基苯基)-1,3,4-噁二唑(b4)、2-[4-(3,3-二甲基三氮烯-1-基)苯基]-5-(2-甲氧基苯基)-1,3,4-噁二唑(b9)、2-[4-(3,3-二甲基三氮烯-1-基)苯基]-5-(3,4-甲叉二氧基苯基)-1,3,4-噁二唑(b10)、2-[4-(3,3-二甲基三氮烯-1-基)苯基]-5-(吡啶-4-基)-1,3,4-噁二唑(b11)对前列腺癌细胞的抑制作用强于典型三氮烯药物达卡巴嗪(DTIC), 其IC50值分别为74.145, 87.790, 87.327 和104.875 μmol/L, 而对胃癌细胞则几乎没有抑制作用. 采用微量肉汤稀释法测试了该类化合物对大肠埃希菌(E. coli.)和金黄葡萄球菌(S. aureus)的抑制作用, 结果显示这类化合物对这两种细菌并没有表现出抑制作用.
雷强 , 秦上尚 , 冯翠宁 , 李佩佩 , 张茜 , 龙跃 . 1,3,4-噁二唑三氮烯衍生物的合成及生物活性测定[J]. 有机化学, 2016 , 36(2) : 406 -411 . DOI: 10.6023/cjoc201507004
11 novel 1,3,4-oxadiazole triazene derivatives were designed and synthesized by combination of triazenes and 1,3,4-oxadiazoles. All the target compounds were characterized by 1H NMR, IR and HRMS. The antitumor activities of all compounds were screened by using thiazolylblue (MTT) assay in vitro, in which MGC803 cell lines and PC-3 cell lines were used as the test cancer cell. The results showed that compounds 2-(4-(3,3-dimethyltriaz-1-en-1- yl)phenyl)-5-(4-methoxy- phenyl)-1,3,4-oxadiazole (b4), 2-(4-(3,3-dimethyltriaz-1-en-1-yl)phenyl)-5-(2-methoxyphenyl)-1,3,4-oxadiazole (b9), 2-(4-(3,3-dimethyltriaz-1-en-1-yl)phenyl)-5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-oxadiazole (b10) and 2-(4-(3,3-dimethyltriaz-1-en-1-yl)phenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazole (b11) exhibited higher activity against PC-3 cell than control compound dacarbazine (DTIC), and their IC50 values were 74.145, 87.790, 87.327 and 104.875 μmol/L, respectively. But all compounds had little inhibition effect on MGC803 cell lines. All synthesized compounds were screened by broth dilution technique for their fungicidal activity against S. aureus and E. coli. The antibacterial activity results showed that all of compounds were inactive.
Key words： triazenes; 1,3,4-oxadiazoles; synthesis; antitumor; antibacterial
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