3,2'-二羟基-4,4'-二甲氧基查尔酮 | 2567-65-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 3,2'-二羟基-4,4'-二甲氧基查尔酮
• 英文名称: 2',3-dihydroxy-4,4'-dimethoxychalcone
• 英文别名: (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one；1-(2-Hydroxy-4-methoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• CAS: 2567-65-9
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: PXZWGNIMAQEYSE-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  3,2'-二羟基-4,4'-二甲氧基查尔酮 在 palladium on activated charcoal 氢气 、 汞 、 锌 作用下， 生成 沙纸宁 E; 2-[3-(3-羟基-4-甲氧基苯基)丙基]-5-甲氧基苯酚
  参考文献：
  名称：

  EIGHT MINOR PHYTOALEXINS FROM DISEASED PAPER MULBERRY

  摘要：

  真菌接种的纸莎草嫩枝皮层组织产生了八种次要的抗真菌化合物：两种黄酮类化合物，分别被命名为 broussinol 和 demethylbroussin；四种 1,3-二苯基丙烷类化合物，被命名为 broussonin C-F；以及两种查耳酮类化合物。文中介绍了这些化合物的分离和结构阐释。

  DOI：

  10.1246/cl.1984.689
• 作为产物：
  描述：

  异香兰素 、 丹皮酚 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到3,2'-二羟基-4,4'-二甲氧基查尔酮
  参考文献：
  名称：

  Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization

  摘要：

  DOI：

  10.1016/j.bioorg.2021.105043

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.
• NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA
  申请人：UNIVERSITÀ DEGLI STUDI DI ROMA "LA SAPIENZA"

  公开号：US20190337916A1

  公开（公告）日：2019-11-07

  Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).
• Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization
  作者：Junjie Yang、Fanjie Hu、Chengjun Guo、Yuqing Liang、Haiying Song、Kui Cheng

  DOI：10.1016/j.bioorg.2021.105043

  日期：2021.9
• EIGHT MINOR PHYTOALEXINS FROM DISEASED PAPER MULBERRY
  作者：Mitsuo Takasugi、Nobuyuki Niino、Shigemitsu Nagao、Masaki Anetai、Tadashi Masamune、Akira Shirata、Kokichi Takahashi

  DOI：10.1246/cl.1984.689

  日期：1984.5.5

  The fungus-inoculated Broussonetia papyrifera shoot cortical tissues produced eight minor antifungal compounds: two flavans named broussinol and demethylbroussin, four 1,3-diphenylpropanes named broussonin C–F, and two chalcones. Isolation and structure elucidation of these compounds are described.

  真菌接种的纸莎草嫩枝皮层组织产生了八种次要的抗真菌化合物：两种黄酮类化合物，分别被命名为 broussinol 和 demethylbroussin；四种 1,3-二苯基丙烷类化合物，被命名为 broussonin C-F；以及两种查耳酮类化合物。文中介绍了这些化合物的分离和结构阐释。