7,2',4'-trimethoxyflavanone | 132351-64-5

• 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',4'-trimethoxyflavanone
• 英文别名: 2-(2,4-dimethoxy-phenyl)-7-methoxy-chroman-4-one；2-(2,4-Dimethoxy-phenyl)-7-methoxy-chroman-4-on；2-(2,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 132351-64-5
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: NBIJGBGFCIDZKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7,2',4'-trimethoxyflavanone 在 硫酸 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以53 mg的产率得到2-(2,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Gao, Jin-Ming; Lu, Jia-Wen; Zhang, An-Ling, Journal of Chemical Research, 2006, # 3, p. 163 - 164

  摘要：

  DOI：
• 作为产物：
  描述：

  丹皮酚 在 barium dihydroxide 、 硫酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 7,2',4'-trimethoxyflavanone
  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

• One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavones
  作者：Takeshi Kinoshita、Koji Ichinose、Ushio Sankawa

  DOI：10.1016/s0040-4039(00)88565-2

  日期：1990.1
• Singh, Om V.; Muthukrishnan; Sunderavadivelu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 12, p. 2575 - 2581
  作者：Singh, Om V.、Muthukrishnan、Sunderavadivelu

  DOI：——

  日期：——
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• v. Kostanecki; Lampe; Triulzi, Chemische Berichte, 1906, vol. 39, p. 93
  作者：v. Kostanecki、Lampe、Triulzi

  DOI：——

  日期：——