3-(benzo[d][1,3]dioxol-5-yl)-7-(benzyloxy)-6-methoxy-4H-chromen-4-one | 58099-58-4

• 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: 3-(benzo[d][1,3]dioxol-5-yl)-7-(benzyloxy)-6-methoxy-4H-chromen-4-one
• 英文别名: 3-benzo[1,3]dioxol-5-yl-7-benzyloxy-6-methoxy-chromen-4-one；3-(1,3-Benzodioxol-5-yl)-6-methoxy-7-phenylmethoxychromen-4-one；3-(1,3-benzodioxol-5-yl)-6-methoxy-7-phenylmethoxychromen-4-one
• CAS: 58099-58-4
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: BLMNBHUYOHNRBR-UHFFFAOYSA-N

物化性质

• 沸点：
  596.4±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.13
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,4-二羟基-5-甲氧基苯乙酮 在 吡啶 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 碘 、 四丁基碘化铵 、 sodium carbonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 乙腈 为溶剂， 反应 62.0h， 生成 3-(benzo[d][1,3]dioxol-5-yl)-7-(benzyloxy)-6-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Structure Optimization of Gatastatin for the Development of γ-Tubulin-Specific Inhibitor

  摘要：

  Gatastatin (O-7-benzyl glaziovianin A) is a gamma-tubulin-specific inhibitor that is used to investigate gamma-tubulin function in cells. We have previously reported that the unsubstituted phenyl ring of the O-7-benzyl group in gatastatin is important for gamma-tubulin inhibition. To obtain further structural information regarding gamma-tubulin inhibition, we synthesized several gatastatin derivatives containing a fixed O-7-benzyl moiety. Modifications of the B-ring resulted in drastic decrease in cytotoxicity, abnormal spindle formation activity, and inhibition of microtubule (MT) nucleation. In contrast, various O-6-alkylated gatastatin derivatives showed potent cytotoxicity, induced abnormal spindle formation, and inhibited MT nucleation. We had previously reported that O-6-benzyl glaziovianin A is a potent alpha/beta-tubulin inhibitor; thus, these new results suggest that the O-6-position restricts affinity for alpha/beta- and gamma-tubulin. Considering that an O-7-benzyl group increases specificity for gamma-tubulin, more potent and specific gamma-tubulin inhibitors can be generated through O-6-modifications of gatastatin.

  DOI：

  10.1021/acsmedchemlett.9b00526