3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone | 1266729-01-4

• 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'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone
• 英文别名: 2-(3-Amino-4-methoxyphenyl)-5-hydroxy-3,6,7,8-tetramethoxychromen-4-one
• CAS: 1266729-01-4
• 化学式: C₂₀H₂₁NO₈
• 分子量: 403.389
• InChiKey: RBTFYFDMKCQMIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone 在 lithium chloride 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以26%的产率得到3'-amino-5,7-dihydroxy-3,6,8,4'-tetramethoxy-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：

  5-hydroxy-3'-nitro-3,6,7,8,4'-pentamethoxy-flavone 在 10% palladium on activated charcoal 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以78%的产率得到3'-amino-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