methyl 2-acetoxy-5-formylbenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-acetoxy-5-formylbenzoate
• 英文别名: 2-acetoxy-5-formyl-benzoic acid methyl ester；2-Acetoxy-5-formyl-benzoesaeure-methylester
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: YAOXGHCNLHZDQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetoxy-5-formylbenzoate 、 4-甲氧基苄基三苯基膦溴化盐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of resveratrol–salicylate hybrid derivatives as CYP1A1 inhibitors

  摘要：

  Resveratrol and aspirin are known to exert potential chemopreventive effects through modulation of numerous targets. Considering that the CYP450 system is responsible for the activation of environmental procarcinogens, the aim of this study was to design a new class of hybrid resveratrol-aspirin derivatives possessing the stilbene and the salicylate scaffolds. Using HepG2 cells, we evaluated (a) the inhibition of TCDD-mediated induction of CYP1A1 exerted by resveratrol-aspirin derivatives using the EROD assay, and (b) CYP1A1 mRNA in vitro. We observed significant inhibition (84%) of CYP1A1 activity and a substantial decrease in CYP1A1 mRNA with compound 3, compared to control. Resveratrol did not exert inhibition under the same experimental conditions. This inhibitory profile was supported by docking studies using the crystal structure of human CYP1A1. The potential effect exerted by compound 3 (the most active), provide preliminary evidence supporting the design of hybrid molecules combining the chemical features of resveratrol and aspirin.

  DOI：

  10.3109/14756366.2014.979347
• 作为产物：
  描述：

  5-甲酰基水杨酸甲酯 、 乙酰氯 生成 methyl 2-acetoxy-5-formylbenzoate
  参考文献：
  名称：

  Wayne; Cohen, Journal of the Chemical Society, 1922, vol. 121, p. 1027

  摘要：

  DOI：