4-Oxo-2-phenylchromen-3-olate;oxovanadium(2+) | 1443102-25-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-Oxo-2-phenylchromen-3-olate;oxovanadium(2+)
• 英文别名: 4-oxo-2-phenylchromen-3-olate;oxovanadium(2+)
• CAS: 1443102-25-7
• 化学式: C₃₀H₁₈O₇V
• 分子量: 541.41
• InChiKey: DJBHNCVGBCIQLS-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-羟基黄酮 、 vanadium (II) sulfate * 7 water 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到4-Oxo-2-phenylchromen-3-olate;oxovanadium(2+)
  参考文献：
  名称：

  A novel insulin mimetic vanadium–flavonol complex: Synthesis, characterization and in vivo evaluation in STZ-induced rats

  摘要：

  Since 1985, when Heyliger et al., first demonstrated a serendipitous discovery that oral administration of 0.8 mg/ml of sodium orthovanadate in drinking water to streptozotocin-induced diabetic rats resulted in normoglycemia, numerous extensive studies have been pursued on the anti-diabetic and insulinomimetic actions of vanadium. The acceptance of vanadium compounds as promising therapeutic antidiabetic agents has been slowed due to the concern for chronic toxicity associated with vanadium accumulation. In order to circumvent the toxic effects of vanadium, we have taken up a combinational approach wherein a novel vanadium flavonol complex was synthesized, characterized and its toxic as well as insulin mimetic potential was evaluated in STZ-induced experimental diabetes in rats. The results indicate that the complex is non-toxic and possess anti-diabetic activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.002

文献信息

• Behavior of the potential antitumor VIVO complexes formed by flavonoid ligands. 1. Coordination modes and geometry in solution and at the physiological pH
  作者：Daniele Sanna、Valeria Ugone、Giuseppe Lubinu、Giovanni Micera、Eugenio Garribba

  DOI：10.1016/j.jinorgbio.2014.07.007

  日期：2014.11

  The coordination modes and geometry assumed in solution by the potent antitumor oxidovanadium(IV) complexes formed by different flavonoids were studied by spectroscopic (Electron Paramagnetic Resonance, EPR) and computational (Density Functional Theory, DFT) methods. A series of bidentate flavonoid ligands (L) with increasing structural complexity was examined, which can involve (CO, O(-)) donors and formation of five- and six-membered chelate rings, or (O(-), O(-)) donors and five-membered chelate rings. The geometry corresponding to these coordination modes can be penta-coordinated, [VOL2], or cis-octahedral, cis-[VOL2(H2O)]. The results show that, at physiological pH, ligands provided with (CO, O(-)) donor set yield cis-octahedral species with "maltol-like" coordination when five-membered chelate rings are formed (as with 3-hydroxyflavone), while penta-coordinated structures with "acetylacetone-like" coordination are preferred when the chelate rings are six-membered (as with chrysin). When both the binding modes are possible, as with morin, the "acetylacetone-like" coordination is observed. For the ligands containing a catecholic donor set, such as 7,8-dihydroxyflavone, baicalein, fisetin, quercetin and rutin, the formation of square pyramidal complexes with (O(-), O(-)) "catechol-like" coordination and five-membered chelate rings is preferred at physiological pH. The determination of the different coordination modes and geometry is important to define the biotransformation in the blood and the interaction of these complexes with the biological membranes.
• A novel insulin mimetic vanadium–flavonol complex: Synthesis, characterization and in vivo evaluation in STZ-induced rats
  作者：Subramanian Iyyam Pillai、Sorimuthu Pillai Subramanian、Muthusamy Kandaswamy

  DOI：10.1016/j.ejmech.2013.02.002

  日期：2013.5

  Since 1985, when Heyliger et al., first demonstrated a serendipitous discovery that oral administration of 0.8 mg/ml of sodium orthovanadate in drinking water to streptozotocin-induced diabetic rats resulted in normoglycemia, numerous extensive studies have been pursued on the anti-diabetic and insulinomimetic actions of vanadium. The acceptance of vanadium compounds as promising therapeutic antidiabetic agents has been slowed due to the concern for chronic toxicity associated with vanadium accumulation. In order to circumvent the toxic effects of vanadium, we have taken up a combinational approach wherein a novel vanadium flavonol complex was synthesized, characterized and its toxic as well as insulin mimetic potential was evaluated in STZ-induced experimental diabetes in rats. The results indicate that the complex is non-toxic and possess anti-diabetic activity. (C) 2013 Elsevier Masson SAS. All rights reserved.