(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one | 36685-61-7

• 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
• 英文名称: (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2-hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one；(E)-2'-hydroxy-2,3,4,4'-tetramethoxychalcone；2'-hydroxy-2,3,4,4'-tetramethoxychalcone
• CAS: 36685-61-7
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: DOMQQVLOFWGMFV-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以52%的产率得到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
• 作为产物：
  描述：

  丹皮酚 、 2,3,4-三甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 73.0h， 以59%的产率得到(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  结构多样的双黄酮类化合物的合成

  摘要：

  合成的双黄酮类化合物与有趣的生物学活性有关，但在药物发现中仍缺乏很好的探索。近年来，目睹了对合成方法的日益增长的兴趣，这些方法可以提供结构新颖的双黄酮类化合物，因此可以更充分地研究此类化合物的生物学用途。在本文中，我们报告了基于铃木-宫浦交叉偶联和醇甲基化的策略，用于合成两类双黄酮类化合物：（i）含有属于不同亚类的类黄酮单体的稀有“杂化”衍生物，以及（ii）同二聚体化合物，其中两个类黄酮单体通过亚甲二氧基连接。

  DOI：

  10.1016/j.tet.2018.05.003

文献信息

• Novel Chalcone Derivatives With Antimitotic Activity
  申请人：Boumendjel Ahcene

  公开号：US20090182058A1

  公开（公告）日：2009-07-16

  The present invention relates to novel chalcone derivatives of formula (I): wherein X, Y, Z, W, RI, R2, R3, R4 and R5 are as defined, said derivatives having antimitotic activity, as well as to pharmaceutical compositions containing such compounds and to their use for making drugs.

  本发明涉及具有抗有丝分裂活性的新型葵花素衍生物的公式(I)：其中X、Y、Z、W、RI、R2、R3、R4和R5如定义所述，以及含有这种化合物的药物组合物，以及其用于制备药物的用途。
• Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents
  作者：Mopur Vijaya Bhaskar Reddy、Hsin-Yi Hung、Ping-Chung Kuo、Guan-Jhong Huang、Yu-Yi Chan、Shiow-Chyn Huang、Shwu-Jen Wu、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmcl.2017.02.038

  日期：2017.4

  Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol

  通过醛醇缩合制备二十一个查耳酮，随后将这些化合物还原，得到相应的二氢查耳酮和1，3-二苯基丙烷衍生物。检查了合成产物对LPS活化的小鼠腹膜巨噬细胞中NO抑制的影响。在测试的化合物中，1,3-二芳基丙烷类似物2-（3-（3,4-二甲氧基苯基）丙基）-5-甲氧基苯酚（3p）对NO的产生表现出最显着的抑制作用。为了研究作用机理，通过免疫印迹研究了3p对iNOS和COX-2蛋白表达的影响。结果得出结论，3p能够通过ERK，p38和JNK减弱NF-κB信号传导而抑制LPS诱导的RAW264.7细胞中的iNOS表达。
• Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure–Activity Relationship
  作者：Ahcène Boumendjel、Julien Boccard、Pierre-Alain Carrupt、Edwige Nicolle、Madeleine Blanc、Annabelle Geze、Luc Choisnard、Denis Wouessidjewe、Eva-Laure Matera、Charles Dumontet

  DOI：10.1021/jm0708331

  日期：2008.4.1

  A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of I I human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
• 1-(2-Hydroxy-4-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  作者：A. Subbiah Pandi、D. Velmurugan、S. Shanmuga Sundara Raj、Hoong-Kun Fun、M. C. Bansal

  DOI：10.1107/s0108270103008679

  日期：2003.6.15

  The title compound, C19H20O6, crystallizes in the centrosymmetric space group P2(1)/c with one molecule in the asymmetric unit. The molecule is approximately planar and the dihedral angle between the phenyl rings is 11.0(1)degrees. The H atoms of the central propenone group are trans. There is an intramolecular O-H...O hydrogen bond and the molecules are crosslinked by four intermolecular C-H...O hydrogen bonds, producing a three-dimensional network.
• ASHIHARA Y.; NAGATA Y.; KUROSAWA K., BULL. CHEM. SOC. JAP. <BCSJ-A8>, 1977, 50, NO 12, 3298-3301
  作者：ASHIHARA Y.、 NAGATA Y.、 KUROSAWA K.

  DOI：——

  日期：——

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