O⁷-demethyl glaziovianin A | 1252801-64-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: O⁷-demethyl glaziovianin A
• 英文别名: 3-(4,7-Dimethoxy-1,3-benzodioxol-5-yl)-7-hydroxy-6-methoxychromen-4-one
• CAS: 1252801-64-1
• 化学式: C₁₉H₁₆O₈
• 分子量: 372.331
• InChiKey: ZGJLPIFVPCFYDU-UHFFFAOYSA-N

物化性质

• 沸点：
  602.6±55.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O⁷-demethyl glaziovianin A 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 (E)-N-(6-aminohexyl)-6-(3-(4,7-dimethoxybenzo[d][1,3]dioxol-5-yl)-6-methoxy-4-oxo-4H-chromen-7-yloxy)hex-4-enamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of the analogues of glaziovianin A, a potent antitumor isoflavone

  摘要：

  Various analogues of glaziovianin A, an antitumor isoflavone, were synthesized, and their biological activities were evaluated. O-7-modified glaziovianin A showed strong cytotoxicity against HeLa S-3 cells. Compared to glaziovianin A, the O-7-benzyl and O-7-propargyl analogues were more cytotoxic against HeLa S-3 cells and more potent M-phase inhibitors. Furthermore, O-7-modified molecular probes of glaziovianin A were synthesized for biological studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.005
• 作为产物：
  描述：

  3-iodo-6-methoxy-7-(tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 为溶剂， 反应 27.5h， 生成 O⁷-demethyl glaziovianin A
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of the analogues of glaziovianin A, a potent antitumor isoflavone

  摘要：

  Various analogues of glaziovianin A, an antitumor isoflavone, were synthesized, and their biological activities were evaluated. O-7-modified glaziovianin A showed strong cytotoxicity against HeLa S-3 cells. Compared to glaziovianin A, the O-7-benzyl and O-7-propargyl analogues were more cytotoxic against HeLa S-3 cells and more potent M-phase inhibitors. Furthermore, O-7-modified molecular probes of glaziovianin A were synthesized for biological studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.005

文献信息

• Practical Synthesis of Glaziovianin A, a Cytotoxic Isoflavone, and Its <i>O</i>⁷-Propargyl Analogue
  作者：Ichiro Hayakawa、Shuya Shioda、Akiyuki Ikedo、Hideo Kigoshi

  DOI：10.1246/bcsj.20130342

  日期：2014.4.15

  Glaziovianin A and its O7-propargyl analogue are potent cytotoxic isoflavones. We found that the O7-propargyl analogue completely arrested cell-cycle progression. We have achieved the large-scale synthesis of glaziovianin A and its O7-propargyl analogue for further in vivo experimentation.

  Glaziovianin A及其O7-炔丙基类似物是强效的细胞毒性异黄酮。我们发现O7-炔丙基类似物能完全阻止细胞周期的进展。我们已经实现了Glaziovianin A及其O7-炔丙基类似物的大规模合成，以供进一步的体内实验研究。
• Structure–Activity Relationship Study of Gatastatin Based on the Topliss Tree Approach
  作者：Ichiro Hayakawa、Hideo Kigoshi、Shuya Shioda、Takumi Chinen、Takeo Usui

  DOI：10.3987/com-18-s(f)16

  日期：——
• Structure–activity relationship study of glaziovianin A against cell cycle progression and spindle formation of HeLa S3 cells
  作者：Akiyuki Ikedo、Ichiro Hayakawa、Takeo Usui、Sayaka Kazami、Hiroyuki Osada、Hideo Kigoshi

  DOI：10.1016/j.bmcl.2010.07.111

  日期：2010.9

  Various derivatives of glaziovianin A, an antitumor isoflavone, were synthesized, and the cytotoxicity of each against HeLa S-3 cells was investigated. Compared to glaziovianin A, the O-7-allyl derivative was found to be more cytotoxic against HeLa S-3 cells and a more potent M-phase inhibitor. (c) 2010 Elsevier Ltd. All rights reserved.