| 摘要: |
| 从松节藻中分离的含卤素化合物表现出显著PTP1B抑制活性。其中BPN效果最佳。为研究BPN侧链基团极性对其抑制活性的影响, 本文以香兰素(1)为起始原料, 经过溴代、氧化、还原、傅克烷基化以及酯化等反应, 成功合成了新化合物2, 3-二溴-1-(2-溴-3, 4-二甲氧基-6-((4-硝基苯氧基)甲基)苯甲基)-4, 5-二甲氧基苯(10)、4-((3-溴-2-(2, 3-二溴-4, 5-二甲氧基苄基)-4, 5-二甲氧基苄基)醚)苯胺(11)、4-((3-溴-2-(2, 3-二溴-4, 5-二甲氧基苄基)-4, 5-二甲氧基苄基)醚)-4-乙酰乙酸(12)和3-溴-2-(2, 3-二溴-4,5-二甲氧基苄基)-4, 5-二甲氧基苯甲醛肟(14)。通过1H-NMR, 13C-NMR等方法对目标产物进行了结构表征。并对化合物进行了PTP1B酶抑制活性的测定, 结果表明化合物侧链极性对PTP1B酶抑制活性有显著影响。 |
| 关键词: 海洋卤代化合物 PTP1B 抑制剂 化学合成 |
| DOI：10.11759/hykx20161210 |
| 分类号: |
| 基金项目:国家自然科学基金项目(41276167); 山东省重点研发计划(2015GGF01039); 青岛市基础研究计划项目(No.14-2-4-35-jch); 国家高层次人才特支计划“万人计划”; 国家海洋实验室“鳌山人才计划” |
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| Investigation of synthesis and PTP1B inhibitory activity of four new halogenated compounds |
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WANG Bao-cheng,WANG Li-jun,JIANG Bo,YANG Meng,SHI Da-yong
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| Abstract: |
| Halogenated compounds separated from Rhodomela confervoides have demonstrated significant protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Of these compounds, the inhibitory activity of BPN is the best. To further investigate the effects of side chain polarity, in this assay we synthesized four new compounds, including (2, 3-dibromo-1-(2-bromo-3, 4-dimethoxy-6- ((4-nitrophenoxy)methyl)benzyl)-4, 5-dimethoxybenzene (10), 4-((3-bromo-2-(2, 3-dibromo-4, 5-dimethoxybenzyl)-4, 5-dimethoxybenzyl)oxy)aniline (11), 4-((3-bromo-2-(2, 3-dibromo-4, 5-dimethoxybenzyl)-4, 5-dimethoxybenzyl)oxy)-4-oxobutanoic acid (12), and 3-bromo-2-(2, 3-dibromo-4, 5-dimethoxybenzyl)-4, 5-dimethoxybenzaldehyde oxime (14)). We tested the inhibitory activity of these compounds against PTP1B and found compound 14 to display better inhibitory activity with appropriate side chain polarity. |
| Key words: Halogenated compounds PTP1B inhibitory activity Chemosynthesis |
