3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde | 910820-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde
• CAS: 910820-95-0
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: FMKWOVWYLDGGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde 、 (4-carboxybutanoyl)hydrazinium hydrochoride 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Z-5-(2-{[3-(4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-2-furyl]methylidene}hydrazino)-5-oxopentanoic acid 、 5-[(2E)-2-[[3-(4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-yl]methylidene]hydrazinyl]-5-oxopentanoic acid
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurans, Potential Scaffolds for Dual-Action Antitumoral Agents

  摘要：

  We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure- activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.

  DOI：

  10.1021/jm060621o
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙酸 在 氢氧化钾 、 18-冠醚-6 、 TEA 、 二异丁基氢化铝 、 三氯化磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.5h， 生成 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurans, Potential Scaffolds for Dual-Action Antitumoral Agents

  摘要：

  We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure- activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.

  DOI：

  10.1021/jm060621o

文献信息

• Synthesis and Cytotoxic Evaluation of Combretafurans, Potential Scaffolds for Dual-Action Antitumoral Agents
  作者：Tracey Pirali、Sara Busacca、Lorena Beltrami、Daniela Imovilli、Francesca Pagliai、Gianluca Miglio、Alberto Massarotti、Luisella Verotta、Gian Cesare Tron、Giovanni Sorba、Armando A. Genazzani

  DOI：10.1021/jm060621o

  日期：2006.8.1

  We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure- activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.