Methyl(E)-3-(2-((E)-3-(2-hydroxy-3-methylphenyl)-2-propenyl)phenyl)-2-propenoate | 263754-54-7

• 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: Methyl(E)-3-(2-((E)-3-(2-hydroxy-3-methylphenyl)-2-propenyl)phenyl)-2-propenoate
• 英文别名: methyl (E)-3-[2-[(E)-3-(2-hydroxy-3-methylphenyl)prop-2-enyl]phenyl]prop-2-enoate
• CAS: 263754-54-7
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: UQHMUWWTEYYOQV-ZFNDVPRISA-N

物化性质

• 沸点：
  466.6±40.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  Methyl(E)-3-(2-((E)-3-(2-hydroxy-3-methylphenyl)-2-propenyl)phenyl)-2-propenoate 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-{2-[(E)-3-(2-Benzyloxy-3-methyl-phenyl)-allyl]-phenyl}-acrylic acid
  参考文献：
  名称：

  Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists

  摘要：

  A series of novel ortho-substituted cinnamic acids have been synthesized, and their binding activity and selectivity on the four prostaglandin E, receptors evaluated. Many of them are very potent and selective EP3 antagonists (K-i 3-10 nM), while compound 9 is a very good and selective EP2 agonist (K-i 8 nM). The biological profile of the EP2 agonist 9 in vivo and the metabolic profile of selected EP3 antagonists are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.051
• 作为产物：
  描述：

  邻溴肉桂酸 在 四丁基氯化铵 palladium diacetate 、 lithium acetate 、 sodium hydride 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 Methyl(E)-3-(2-((E)-3-(2-hydroxy-3-methylphenyl)-2-propenyl)phenyl)-2-propenoate
  参考文献：
  名称：

  Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists

  摘要：

  A series of novel ortho-substituted cinnamic acids have been synthesized, and their binding activity and selectivity on the four prostaglandin E, receptors evaluated. Many of them are very potent and selective EP3 antagonists (K-i 3-10 nM), while compound 9 is a very good and selective EP2 agonist (K-i 8 nM). The biological profile of the EP2 agonist 9 in vivo and the metabolic profile of selected EP3 antagonists are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.051

文献信息

• Prostaglandin receptor ligands
  申请人：Merck Frosst Canada & Co.

  公开号：US06211197B1

  公开（公告）日：2001-04-03

  Compounds and methods for treating prostaglandin mediated diseases, and certain pharmaceutical compositions thereof are disclosed. The compounds are represented by formula II: Ar1—W—Ar2—X—Q  II The compounds of the invention are structurally different from NSAIDs and opiates, and are antagonists of the pain and inflammatory effects of E-type prostaglandins.

  本发明揭示了用于治疗前列腺素介导疾病的化合物和方法，以及某些制药组合物。这些化合物由式II表示：Ar1—W—Ar2—X—Q。该发明的化合物在结构上与非甾体类抗炎药和阿片类药物不同，是E型前列腺素的疼痛和炎症作用的拮抗剂。
• US6211197B1
  申请人：——

  公开号：US6211197B1

  公开（公告）日：2001-04-03