3'-formyl-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone | 1266729-21-8

• 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: 3'-formyl-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone
• 英文别名: 5-(5-Hydroxy-3,6,7,8-tetramethoxy-4-oxochromen-2-yl)-2-methoxybenzaldehyde
• CAS: 1266729-21-8
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: WKPRZSYGIBYROC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-formyl-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone 在 甲酸 、 盐酸羟胺 作用下， 反应 2.0h， 以56%的产率得到3'-cyano-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone
  参考文献：
  名称：

  Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.

  摘要：

  Eighteen new analogues of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxy-flavone, a potent natural cytotoxic and antimitotic flavone, were synthesized from calycopterin, the major flavonoid of Calycopteris floribunda Lamk., a traditional Asian medicinal plant. One of them, the 3'-amino substituted analogue, displayed almost the same activity as the reference compound. Pharmacomodulation at C-3' on the B-ring, and at C-5,6,7 and 8 on the A-ring allowed to refine structure-activity relationships within the cytotoxic flavones series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.035
• 作为产物：
  描述：

  卡来可黄素 在 potassium hydrogencarbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 3'-formyl-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone
  参考文献：
  名称：

  Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.

  摘要：

  Eighteen new analogues of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxy-flavone, a potent natural cytotoxic and antimitotic flavone, were synthesized from calycopterin, the major flavonoid of Calycopteris floribunda Lamk., a traditional Asian medicinal plant. One of them, the 3'-amino substituted analogue, displayed almost the same activity as the reference compound. Pharmacomodulation at C-3' on the B-ring, and at C-5,6,7 and 8 on the A-ring allowed to refine structure-activity relationships within the cytotoxic flavones series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.035

文献信息

• Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.
  作者：Guy Lewin、Narayan Bhat Shridhar、Geneviève Aubert、Sylviane Thoret、Joëlle Dubois、Thierry Cresteil

  DOI：10.1016/j.bmc.2010.11.035

  日期：2011.1

  Eighteen new analogues of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxy-flavone, a potent natural cytotoxic and antimitotic flavone, were synthesized from calycopterin, the major flavonoid of Calycopteris floribunda Lamk., a traditional Asian medicinal plant. One of them, the 3'-amino substituted analogue, displayed almost the same activity as the reference compound. Pharmacomodulation at C-3' on the B-ring, and at C-5,6,7 and 8 on the A-ring allowed to refine structure-activity relationships within the cytotoxic flavones series. (C) 2010 Elsevier Ltd. All rights reserved.