5-hydroxy-3'-nitro-6,7,8,4'-tetramethoxyisoflavone | 1356700-18-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5-hydroxy-3'-nitro-6,7,8,4'-tetramethoxyisoflavone
• 英文别名: 5-Hydroxy-6,7,8-trimethoxy-3-(4-methoxy-3-nitrophenyl)chromen-4-one
• CAS: 1356700-18-9
• 化学式: C₁₉H₁₇NO₉
• 分子量: 403.345
• InChiKey: FMQIVIBGEJPRTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 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：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3'-nitro-6,7,8,4'-tetramethoxyisoflavone 在 palladium 10% on activated carbon 、 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 1.5h， 以5.5 mg的产率得到3'-amino-5-hydroxy-6,7,8,4'-tetramethoxyisoflavone
  参考文献：
  名称：

  Influence of the skeleton on the cytotoxicity of flavonoids

  摘要：

  Analogs of 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone, a strongly cytotoxic and antimitotic semisynthetic flavone, were synthesized in the aurone, isoflavone and isoflavanone series. Comparison of the biological activity of these new compounds with the reference showed a potent cytotoxicity only in the flavone series. Influence of the hydroxy group (at C-5 in flavones, at C-4 in aurones) on the cytotoxicity, known to be favorable in flavones, was found to be detrimental in aurones. This observation was related to the hydrogen bonding formed with the carbonyl group, strong in the flavones, but of weak intensity in the aurones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.038
• 作为产物：
  描述：

  2,3,4,5-tetramethoxy-6-(3-(4-methoxy-3-nitrophenyl)acryloyl)phenyl benzoate 在 aluminum tri-bromide 、 碘苯二乙酸 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 62.33h， 生成 5-hydroxy-3'-nitro-6,7,8,4'-tetramethoxyisoflavone
  参考文献：
  名称：

  Influence of the skeleton on the cytotoxicity of flavonoids

  摘要：

  Analogs of 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone, a strongly cytotoxic and antimitotic semisynthetic flavone, were synthesized in the aurone, isoflavone and isoflavanone series. Comparison of the biological activity of these new compounds with the reference showed a potent cytotoxicity only in the flavone series. Influence of the hydroxy group (at C-5 in flavones, at C-4 in aurones) on the cytotoxicity, known to be favorable in flavones, was found to be detrimental in aurones. This observation was related to the hydrogen bonding formed with the carbonyl group, strong in the flavones, but of weak intensity in the aurones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.038

文献信息

• Influence of the skeleton on the cytotoxicity of flavonoids
  作者：Guy Lewin、Geneviève Aubert、Sylviane Thoret、Joëlle Dubois、Thierry Cresteil

  DOI：10.1016/j.bmc.2011.12.038

  日期：2012.2

  Analogs of 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone, a strongly cytotoxic and antimitotic semisynthetic flavone, were synthesized in the aurone, isoflavone and isoflavanone series. Comparison of the biological activity of these new compounds with the reference showed a potent cytotoxicity only in the flavone series. Influence of the hydroxy group (at C-5 in flavones, at C-4 in aurones) on the cytotoxicity, known to be favorable in flavones, was found to be detrimental in aurones. This observation was related to the hydrogen bonding formed with the carbonyl group, strong in the flavones, but of weak intensity in the aurones. (C) 2011 Elsevier Ltd. All rights reserved.