(E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl)prop-2-en-1-one | 1622397-82-3

• 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)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
• CAS: 1622397-82-3
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: FCMITIPRVNTWRD-JXMROGBWSA-N

物化性质

• 沸点：
  572.7±50.0 °C(predicted)
• 密度：
  1.138±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl)prop-2-en-1-one 在 mercury(II) diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以44%的产率得到(2Z)-2-[(3,4-dimethoxyphenyl)methylene]-6-methoxy-5-(3-methylbut-2-enyl)benzofuran-3-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：

  丹皮酚 在 potassium carbonate 、 N,N-二甲基苯胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl)prop-2-en-1-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

文献信息

• 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.