glaziovianin A

• 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: glaziovianin A
• 英文别名: 6,7-dimethoxy-3-(4,7-dimethoxy-1,3-benzodioxol-5-yl)-4H-chromen-4-one；3-(4,7-dimethoxy-1,3-benzodioxol-5-yl)-6,7-dimethoxychromen-4-one
• 化学式: C₂₀H₁₈O₈
• mdl: MFCD30711493
• 分子量: 386.358
• InChiKey: GUSKXWBKZXULSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  glaziovianin A 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以31%的产率得到3-(6-Bromo-4,7-dimethoxy-1,3-benzodioxol-5-yl)-6,7-dimethoxychromen-4-one
  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：

  洋芹脑 在 2-吡啶甲酸 、 copper(l) iodide 、 三氟化硼乙醚 、 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.67h， 生成 glaziovianin A
  参考文献：
  名称：

  从莳萝和欧芹提取物中高效合成Glaziovianin A异黄酮系列及其体外/体内抗有丝分裂活性

  摘要：

  开发了一种简明的六步方案，从莳萝和香菜种子中容易获得的植物代谢物开始合成异黄酮glaziovianin A（GVA）及其烷氧基苯基衍生物9。反应顺序包括将关键的中间环氧化物7有效转化为相应的β-酮醛8，然后将它们的Cu（I）介导的环化反应转化为目标序列9。使用一组七种人类癌细胞系和体内海胆胚胎测定法评估了GVA及其衍生物的生物活性。两个筛选平台均证实了亲本GVA（9cg）及其烷氧基衍生物。结构与活性之间的关系研究表明，分别被三甲氧基和莳萝酚衍生的B环取代的化合物9cd和9cf的活性低于母体9cg。在评估的人类癌细胞系中，A375黑色素瘤细胞系对被测分子最敏感。值得注意的是，目标化合物对浓度高达10μM的人外周血单核细胞没有细胞毒性。海胆测定的表型读数明确表明异黄酮9cg，9cd和9cf具有直接的微管破坏作用。

  DOI：

  10.1021/acs.jnatprod.6b00173

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。
• Synthesis of Isoflavones by Tandem Demethylation and Ring-Opening/Cyclization of Methoxybenzoylbenzofurans
  作者：Phaladi Kunyane、Molahlehi S. Sonopo、Mamoalosi A. Selepe

  DOI：10.1021/acs.jnatprod.9b00681

  日期：2019.11.22

  The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated

  描述了通过涉及脱保护和开环/环化的分子内级联意外地将苯甲酰基苯并呋喃转化为异黄酮。这是在对苯甲酰基苯并呋喃可能转化为香豆色酮的研究中发现的。这条路线从苯乙酮和苯醌分两个主要步骤提供了异黄酮。该转化通过合成不同取代的异黄酮衍生物得到了验证，并进一步应用于潜在的抗癌先导化合物glaziovianin A（1）的简明合成。
• Synthesis of Glaziovianin A: A Potent Antitumor Isoflavone
  作者：Ichiro Hayakawa、Akiyuki Ikedo、Hideo Kigoshi

  DOI：10.1246/cl.2007.1382

  日期：2007.11.5

  Glaziovianin A (1) is a novel isoflavone derivative isolated from the leaves of the Brazilian tree Astelia glazioviana. Glaziovianin A (1) showed cytotoxic activity and was suggested to be an inhibitor of tubulin polymerization. We achieved the total synthesis of glaziovianin A (1) by using the Suzuki–Miyaura coupling as a key step.

  Glaziovianin A (1) 是一种从巴西树 Astelia glazioviana 的叶子中分离出来的新型异黄酮衍生物。 Glaziovianin A (1) 显示出细胞毒活性，被认为是微管蛋白聚合的抑制剂。我们以 Suzuki-Miyaura 偶联为关键步骤，实现了 Glaziovianin A (1) 的全合成。
• Synthesis of analogues of natural antimitotic glaziovianin A based on dill and parsley seed essential oils
  作者：Dmitry V. Tsyganov、Leonid D. Konyushkin、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.mencom.2016.07.005

  日期：2016.7

  Glaziovianin A and its analogues were synthesized in six steps starting from allylpolyalkoxybenzenes separated from essential oils of dill (Anetum graviolens) and parsley (Petroselinum sativum) seeds.
• Design, synthesis, and biological evaluation of the analogues of glaziovianin A, a potent antitumor isoflavone
  作者：Ichiro Hayakawa、Akiyuki Ikedo、Takumi Chinen、Takeo Usui、Hideo Kigoshi

  DOI：10.1016/j.bmc.2012.08.005

  日期：2012.10

  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.