| 朱周静,王艳娇,仝红娟,徐小娜,刘斌.化学通报,2023,86(5):607-611. |
| 1-异丙基-3-异丙烯基-1H-吡唑并[3,4-d]嘧啶-4-胺的合成、表征及抗肿瘤活性 |
| Synthesis, Characterization and Antitumor activity of 1-Isopropyl-3-(Prop-1- en-2-yl)-1H-Pyrazolo[3, 4-d]pyrimidin-4-Amine |
| 投稿时间：2022-09-15 修订日期：2022-10-28 |
| DOI： |
| 中文关键词: 吡唑并[3,4-d]嘧啶衍生物 Suzuki偶联反应 晶体结构 抗肿瘤活性 |
| 英文关键词:pyrazolo[3,4-d]pyrimidins Suzuki coupling reaction crystal structure antitumor activity |
| 基金项目:陕西省自然科学基础研究计划项目(2021JQ-885)、咸阳市分子影像与药物合成重点实验室项目(2021QXNL-PT-0008)和陕西国际商贸学院“中药药效物质研究”创新团队建设项目(SSY18TD01)资助 |
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| 中文摘要: |
| 以3-碘-1H-吡唑并[3,4-d]嘧啶-4-胺(2)为原料,经过N-烷基化、Suzuki偶联反应得到目标化合物1-异丙基-3-(异丙烯基)-1H-吡唑并[3,4-d]嘧啶-4-胺(1),两步反应总收率57.0 %。产物及中间体结构经1H NMR、13C NMR、ESI-MS以及X-射线单晶衍射进行表征。并对该Suzuki反应条件进行研究,确定最佳条件为：Pd(dppf)Cl2的用量为n (Pd(dppf)Cl2) : n (化合物3) = 0.06 : 1；物料比为n(异丙烯基硼酸): n(化合物3)= 1.6 : 1；反应溶剂为N,N-二甲基甲酰胺；反应温度为100 ℃；反应时间2 h,在最佳反应条件下,该Suzuki偶联反应收率达到68.2 %。体外抗肿瘤活性测试表明,产物(1)对MCF-7、A549、PC-3、HepG2和SGC-7901增殖均有明显的抑制活性,特别抑制MCF-7的IC50值达到10.6 μmol?L-1。 |
| 英文摘要: |
| The target compound of 1-isopropyl-3-(prop-1-en-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1) was synthesized by N-alkylation and Suzuki coupling reaction from 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2), the total yield of the two-step reaction was 57.0%. The product and intermediates were characterized by 1H NMR, 13C NMR and ESI-MS and X-ray diffraction analysis. The optimum Suzuki reaction conditions were determined as follows: the dosage of Pd(dppf)Cl2 was n (Pd(dppf)Cl2) : n (compound 3) = 0.06 : 1; the mole ratio of n (prop-1-en-2-ylboronic acid 4) : n (compound 3) = 1.6 : 1; the reaction in N,N-dimethylformamide at 100℃ for 2 h, the yield of Suzuki coupling reaction was 68.2% under this conditions. In vitro anti-tumor activity test showed that the product (1) had significant inhibitory activity on the proliferation of MCF-7, A549, PC-3, Hepg2 and SGC-7901, especially the IC50 of MCF-7 was 10.6 μmol?L-1. |
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