3'-amino-5,6-dihydroxy-3,7,8,4'-tetramethoxy-flavone | 1266729-35-4

• 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-5,6-dihydroxy-3,7,8,4'-tetramethoxy-flavone
• 英文别名: 2-(3-Amino-4-methoxyphenyl)-5,6-dihydroxy-3,7,8-trimethoxychromen-4-one
• CAS: 1266729-35-4
• 化学式: C₁₉H₁₉NO₈
• 分子量: 389.362
• InChiKey: LBLZVWVKDFMTMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  卡来可黄素 在 硝酸 、 三氟乙酸 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.4h， 生成 3'-amino-5,8-dihydroxy-3,6,7,4'-tetramethoxy-flavone 、 3'-amino-5,6-dihydroxy-3,7,8,4'-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

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.