4,4'-(1E,1'E)-2,2'-(1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl)bis(2-methoxy-6-(3-methylbut-2-enyl)phenol) | 1616504-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,4'-(1E,1'E)-2,2'-(1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl)bis(2-methoxy-6-(3-methylbut-2-enyl)phenol)
• 英文别名: 4-[(E)-2-[3-[(E)-2-[4-hydroxy-3-methoxy-5-(3-methylbut-2-enyl)phenyl]ethenyl]-1H-pyrazol-5-yl]ethenyl]-2-methoxy-6-(3-methylbut-2-enyl)phenol
• CAS: 1616504-29-0
• 化学式: C₃₁H₃₆N₂O₄
• 分子量: 500.638
• InChiKey: QDPLDWHKADLDOC-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  87.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5',5''-diprenylcurcumin 在 一水合肼 、 溶剂黄146 作用下， 以80%的产率得到4,4'-(1E,1'E)-2,2'-(1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl)bis(2-methoxy-6-(3-methylbut-2-enyl)phenol)
  参考文献：
  名称：

  SAR Studies on Curcumin’s Pro-inflammatory Targets: Discovery of Prenylated Pyrazolocurcuminoids as Potent and Selective Novel Inhibitors of 5-Lipoxygenase

  摘要：

  The anticarcinogenic and anti-inflammatory properties of curcumin have been extensively investigated, identifying prostaglandin E-2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO), key enzymes linking inflammation with cancer, as high affinity targets. A comparative structure-activity study revealed three modifications dissecting mPGES-1/5-LO inhibition, namely (i) truncation of the acidic, enolized dicarbonyl moiety and/or replacement by pyrazole, (ii) hydrogenation of the interaryl linker, and (iii) (dihydro)prenylation. The prenylated pyrazole analogue 11 selectively inhibited 5-LO, outperforming curcumin by a factor of up to 50, and impaired zymosan-induced mouse peritonitis along with reduced 5-LO product levels. Other pro-inflammatory targets of curcumin (ie., mPGES-1, cyclooxygenases, 12/15-LOs, nuclear factor-kappa B, nuclear factor-erythroid 2-related factor-2, and signal transducer and activator of transcription 3) were hardly affected by 11. The strict structural requirements for mPGES-1 and 5-LO inhibition strongly suggest that specific interactions rather than redox or membrane effects underlie the inhibition of mPGES-1 and 5-LO by curcumin.

  DOI：

  10.1021/jm500308c