1,2,3-trimethoxy-5-[(4-methoxyphenyl)selanyl]benzene | 1433974-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,3-trimethoxy-5-[(4-methoxyphenyl)selanyl]benzene
• 英文别名: 1,2,3-trimethoxy-5-((4-methoxyphenyl)seleno)benzene；(4-methoxyphenyl)(3,4,5-trimethoxyphenyl)selane；1,2,3-Trimethoxy-5-(4-methoxyphenyl)selanylbenzene；1,2,3-trimethoxy-5-(4-methoxyphenyl)selanylbenzene
• CAS: 1433974-37-8
• 化学式: C₁₆H₁₈O₄Se
• 分子量: 353.277
• InChiKey: KAXFQBKENUGFCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  bis(4-methoxyphenyl)diselenide 、 3,4,5-三甲氧基苯硼酸 在 tetrabutylammonium tetrafluoroborate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以84%的产率得到1,2,3-trimethoxy-5-[(4-methoxyphenyl)selanyl]benzene
  参考文献：
  名称：

  用二硒化物试剂电化学锰促进硼酸自由基硒化

  摘要：

  建立了硼酸和二硒化物试剂之间强大且环保的电化学锰促进的自由基硒化反应。该电化学协议使用易于获得的材料为一系列有价值的有机硒化合物提供了一种实际适用的方法。机械实验表明，通过二硒化物的直接或间接电化学氧化形成的硒自由基可能是该转化中的关键物种。

  DOI：

  10.1021/acs.orglett.2c00607

文献信息

• An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
  作者：Zhengjiang Fu、Jian Yin、Dongdong He、Xuezheng Yi、Shengmei Guo、Hu Cai

  DOI：10.1039/d1gc02962b

  日期：——

  An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bioactive molecules and gram-scale transformation have been performed to highlight the synthetic utility of the protocol. CV (cyclic voltammetry) experiment

  在没有金属催化剂和外部氧化剂的电化学条件下，建立了一种通过广泛使用的芳基硼酸的脱硼硒基化合成芳基硒醚的有效方案。已经进行了生物活性分子的合成和克级转化，以突出该协议的合成效用。CV（循环伏安法）实验表明，在标准条件下，二硒化物的阳极氧化发生在芳基硼酸底物的阳极氧化之前。
• Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity
  作者：Edson dos A. dos Santos、Ernest Hamel、Ruoli Bai、James C. Burnett、Camila Santos Suniga Tozatti、Danielle Bogo、Renata T. Perdomo、Alexandra M.M. Antunes、M. Matilde Marques、Maria de F.C. Matos、Dênis P. de Lima

  DOI：10.1016/j.bmcl.2013.06.009

  日期：2013.8

  We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, and its prodrugs combretastatin A-4 phosphate (CA-4P) and combretastatin A-1 phosphate (CA-1P) are being investigated as antitumor agents that cause tumor vascular collapse in addition to their activity as cytotoxic compounds. Here we report the preparation of two sulfur analogs and one selenium analog of CA-4. All synthesized compounds, as well as several synthetic intermediates, were evaluated for inhibition of tubulin polymerization and for cytotoxic activity in human cancer cells. Compounds 3 and 4 were active at nM concentration against MCF-7 breast cancer cells. As inhibitors of tubulin polymerization, both 3 and 4 were more active than CA-4 itself. In addition, 4 was the most active of these agents against 786, HT-29 and PC-3 cancer cells. Molecular modeling binding studies are also reported for compounds 1, 3, 4 and CA-4 to tubulin within the colchicine site. (C) 2013 Elsevier Ltd. All rights reserved.