(Z)-3,4,5-trimethoxy-β-iodostyrene | 1388628-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3,4,5-trimethoxy-β-iodostyrene
• 英文别名: 5-[(Z)-2-iodoethenyl]-1,2,3-trimethoxybenzene
• CAS: 1388628-51-0
• 化学式: C₁₁H₁₃IO₃
• 分子量: 320.127
• InChiKey: FXQXOPXERFHNPV-PLNGDYQASA-N

物化性质

• 沸点：
  365.6±42.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3,4,5-trimethoxy-β-iodostyrene 、 2-羟基-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)苯甲醛 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 20.33h， 以54%的产率得到4-formyl-3-hydroxy-3′,4′,5′-trimethoxy-(Z)-stilbene
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684
• 作为产物：
  描述：

  碘甲基-三苯基-碘化磷 、 3,4,5-三甲氧基苯甲醛 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以72%的产率得到(Z)-3,4,5-trimethoxy-β-iodostyrene
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684

文献信息

• New Method of Synthesis and Biological Evaluation of Some Combretastatin A-4 Analogues
  作者：Andrei Gavryushin、Yulia Malysheva、Sebastien Combes、Alexey Fedorov、Paul Knochel

  DOI：10.1055/s-0031-1290899

  日期：2012.5

  A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50 = 0.022-10.31 mu M).