(E)-1-(2-hydroxy-4-methoxyphenyl)-3-p-tolylprop-2-en-1-one | 137109-37-6

• 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-p-tolylprop-2-en-1-one
• 英文别名: 2'-Hydroxy-4'-methoxy-4-methylbenzalacetophenon；(2E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one；(E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 137109-37-6
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: RJXHSDFJYBWDGV-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-4-methoxyphenyl)-3-p-tolylprop-2-en-1-one 在 双氧水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 (E)-3-(3,7-dimethylocta-2,6-dienyloxy)-7-methoxy-2-p-tolyl-4H-chromen-4-one
  参考文献：
  名称：

  Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

  摘要：

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.

  DOI：

  10.1016/j.bmcl.2014.06.061
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (E)-1-(2-hydroxy-4-methoxyphenyl)-3-p-tolylprop-2-en-1-one
  参考文献：
  名称：

  Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

  摘要：

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.087

文献信息

• CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF
  申请人：Cushman Mark S.

  公开号：US20100099755A1

  公开（公告）日：2010-04-22

  Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

  本文描述了替代黄酮类化合物和黄酮类化合物的药物配方。还描述了制备黄酮类化合物的过程，以及使用所述黄酮类化合物或其药物配方治疗哺乳动物癌症的方法。
• US8946287B2
  申请人：——

  公开号：US8946287B2

  公开（公告）日：2015-02-03
• Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
  作者：Kamal Rullah、Mohd Fadhlizil Fasihi Mohd Aluwi、Bohari M. Yamin、Mohd Nazri Abdul Bahari、Leong Sze Wei、Syahida Ahmad、Faridah Abas、Nor Hadiani Ismail、Ibrahim Jantan、Lam Kok Wai

  DOI：10.1016/j.bmcl.2014.06.061

  日期：2014.8

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.
• Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives
  作者：Tran Thanh Dao、Yeon Sook Chi、Jeongsoo Kim、Hyun Pyo Kim、Sanghee Kim、Haeil Park

  DOI：10.1016/j.bmcl.2003.12.087

  日期：2004.3

  A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3',4'-dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production. (C) 2004 Elsevier Ltd. All rights reserved.