7,2',3',4'-tetramethoxyflavanone | 445285-03-0

• 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: 7,2',3',4'-tetramethoxyflavanone
• 英文别名: 7-Methoxy-2-(2,3,4-trimethoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 445285-03-0
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: HXYUOYQBJCJYOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,2',3',4'-tetramethoxyflavanone 在 碘 、 potassium acetate 、 溶剂黄146 作用下， 反应 2.0h， 生成 7,2',3',4'-tetramethoxyflavone
  参考文献：
  名称：

  Two New 5-Deoxyflavonoids from Calliandra inermis

  摘要：

  两种新的 5-脱氧黄酮类化合物，7,2',3',4'-四甲氧基黄酮 (1) 和 7,2',3',4'-四甲氧基黄酮 (2) 以及已知的黄酮 7,4'-二甲氧基-3 '-羟基黄酮 (3) 是从 Calliandra inermis 的全草中分离出来的。这些新化合物的结构通过高分辨率电子轰击质谱 (HR-EI-MS) 以及 1D 和 2D-​​NMR 光谱研究来阐明，包括 1H-1H 相关光谱 (COSY)、异核单量子相干 (HSQC)、异核多重键连接（HMBC）和核奥沃豪瑟增强光谱（NOESY）。

  DOI：

  10.1248/cpb.52.974
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 barium dihydroxide 、 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 7,2',3',4'-tetramethoxyflavanone
  参考文献：
  名称：

  摘要：

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

  DOI：

  10.1023/a:1014490817731

文献信息

• ——
  作者：Christelle Pouget、Catherine Fagnere、Jean‐Philippe Basly、Anne‐Elise Besson、Yves Champavier、Gerard Habrioux、Albert‐Jose Chulia

  DOI：10.1023/a:1014490817731

  日期：——

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.
• Two New 5-Deoxyflavonoids from Calliandra inermis
  作者：Muchchintala Maheswara、Yerra Koteswara Rao、Vidavalur Siddaiah、Chunduri Venkata Rao、Kasi Viswanatham Somayajulu、Fu Tyan Lin

  DOI：10.1248/cpb.52.974

  日期：——

  Two new 5-deoxyflavonoids, 7,2′,3′,4′-tetramethoxyflavone (1) and 7,2′,3′,4′-tetramethoxyflavanone (2) together with a known flavone 7,4′-dimethoxy-3′-hydroxyflavone (3) were isolated from the whole plant of Calliandra inermis. The structures of these new compounds were elucidated by high resolution electron impact mass spectrometry (HR-EI-MS) and 1D and 2D-NMR spectral studies including 1H–1H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser enhancement spectroscopy (NOESY).

  两种新的 5-脱氧黄酮类化合物，7,2',3',4'-四甲氧基黄酮 (1) 和 7,2',3',4'-四甲氧基黄酮 (2) 以及已知的黄酮 7,4'-二甲氧基-3 '-羟基黄酮 (3) 是从 Calliandra inermis 的全草中分离出来的。这些新化合物的结构通过高分辨率电子轰击质谱 (HR-EI-MS) 以及 1D 和 2D-​​NMR 光谱研究来阐明，包括 1H-1H 相关光谱 (COSY)、异核单量子相干 (HSQC)、异核多重键连接（HMBC）和核奥沃豪瑟增强光谱（NOESY）。