(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one

• 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-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃FO₃
• 分子量: 272.276
• InChiKey: WFEWRCPZGFCBCS-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one 以 乙醇 为溶剂， 以42%的产率得到2-(4-fluorophenyl)-7-methoxychroman-4-one
  参考文献：
  名称：

  Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

  摘要：

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。

  DOI：

  10.1039/c4ob00398e
• 作为产物：
  描述：

  2-(4-fluorophenyl)-7-methoxychroman-4-one 以 乙醇 为溶剂， 生成 (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

  摘要：

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。

  DOI：

  10.1039/c4ob00398e

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.
• Chalcones, inhibitors for topoisomerase I and cathepsin B and L, as potential anti-cancer agents
  作者：Seok-Ho Kim、Eunyoung Lee、Kyung Hye Baek、Han Byeol Kwon、Hyunjung Woo、Eung-Seok Lee、Youngjoo Kwon、Younghwa Na

  DOI：10.1016/j.bmcl.2013.03.106

  日期：2013.6

  In order to diversify the pharmacological activity of chalcones and extend the scaffold of topoisomerase and cathepsins B and L inhibitors, we have designed and synthesized total 18 chalcone compounds and tested their biological activity. In the topoisomerase inhibition test, most analogues in group III and IV except compound 11 exhibited more efficient topoisomerase I inhibitory activity than camptothecin at 20 lM. Compounds 15, 16 and 18 in group IV showed significant cathepsin B and L inhibitory activity. Among the compounds, compound 15 was most active with IC50 values of 1.81 +/- 0.05 mu M on cathepsin B and 3.15 +/- 0.07 mu M on cathepsin L, respectively. Compound 15 also showed most potent cytotoxic activity against T47D and SNU638 cells with IC50 values of 1.37 +/- 0.05 mu M and 0.62 +/- 0.01 mu M, respectively. Overall, although more compounds should be tested and analyzed for clear SAR against topoisomerase I and cathepsin B and L, compound 15 showed consistent inhibitory ability on the tested assays, which can implicate the cytotoxic activity of compound 15 on topoisomerase I and cathepsin B and L inhibitory pathways. (C) 2013 Elsevier Ltd. All rights reserved.
• A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation
  作者：Michael Lorenz、M. Shahjahan Kabir、James M. Cook

  DOI：10.1016/j.tetlet.2009.12.107

  日期：2010.2

  A general route for the synthesis of biologically important flavones is reported via a two step sequence employing a catalytic Wacker-Cook oxidation(4b) as the key step. (C) 2009 Elsevier Ltd. All rights reserved.
• Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold
  作者：Brian M. Muller、Jesse Mai、Reid A. Yocum、Marc J. Adler

  DOI：10.1039/c4ob00398e

  日期：——

  The impact of substitution on a novel colorimetric dynamic covalent switching scaffold was investigated using UV/Vis and NMR spectroscopy.

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。