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目的以异甘草素(ILG)为先导化合物进行化学合成其衍生物3-甲氧基异甘草素(3-MO-ILG),探讨其体外抗宫颈癌活性。方法采用硼酸催化高温法、羟基保护法、微波辅助碱催化法3种方法进行羟醛缩合反应而制备目标化合物;以人宫颈癌Si Ha细胞为体外模型,用3-(4,5-二甲基噻唑-2)-2,5-二苯基四氮唑溴盐(MTT)法测定对癌细胞增长的抑制率;用流式细胞仪测定促进癌细胞凋亡作用,以顺铂作为阳性对照组。结果用硼酸催化高温法、羟基保护法、微波辅助碱催化法3种方法所得到的3-甲氧基异甘草素产率分别为8.9%、9.27%和57.60%。3-甲氧基异甘草素对Si Ha细胞具有较强抑制增殖作用,当药物浓度为20~150μg/m L、作用时间为24 h时,其抑制率可达93.5%;当作用时间达到72 h时,抑制率最强。3-甲氧基异甘草素在100μg/m L时,对Si Ha细胞早期凋亡率为38.6%,晚期凋亡率为1.4%,具有明显的促细胞凋亡作用。结论微波辅助碱催化方法在查尔酮类化合物的合成中具有产率较高的方法。3-甲氧基异甘草素对Si Ha细胞具有较强抑制增殖作用,并且具有明显浓度和时间依赖性;同时对Si Ha细胞具有明显的促细胞凋亡作用。
OBJECTIVE To investigate the anti-cervical cancer activity of 3-methoxyisoflavone (3-MO-ILG), a derivative of isoliquiritigenin (ILG), in vitro. Methods The target compounds were prepared by the aldol condensation reaction with boric acid catalyzed high temperature method, hydroxyl protective method and microwave assisted basic catalysis method. The human cervical cancer Si Ha cells were used as in vitro models, The inhibitory rate of cancer cell growth was determined by MTT assay. The apoptosis of cancer cells was detected by flow cytometry. Cisplatin was used as a positive control group. Results The yields of 3-methoxyisothyridium were 3%, 9.27% and 57.60%, respectively, which were obtained by boric acid catalyzed high temperature method, hydroxyl protection method and microwave assisted basic catalysis method. 3-Methoxy isoliquiritigenin has a strong inhibitory effect on proliferation of Si Ha cells. When the drug concentration is 20-150 μg / m L and the action time is 24 h, the inhibition rate can reach 93.5%. When the action time reaches 72 h, the inhibition rate is strongest. At the concentration of 100μg / mL, the early apoptotic rate of Si Ha cells was 38.6% and the late apoptotic rate was 1.4%, which indicated that 3-methoxyisothyridium had obvious pro-apoptotic effects. Conclusion The microwave-assisted alkaline catalysis method has higher yield in the synthesis of chalcones. 3-Methoxy isoliquiritigenin has a strong inhibitory effect on proliferation of Si Ha cells in a concentration-dependent and time-dependent manner. At the same time, 3-methoxyisothymil has obvious pro-apoptotic effects on Si Ha cells.