(E)-3-(2-{(E)-3-[2-(2,6-Dichloro-benzyloxy)-3-methyl-phenyl]-allyl}-phenyl)-acrylic acid methyl ester | 263754-64-9

• 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-(2-{(E)-3-[2-(2,6-Dichloro-benzyloxy)-3-methyl-phenyl]-allyl}-phenyl)-acrylic acid methyl ester
• 英文别名: methyl (E)-3-[2-[(E)-3-[2-[(2,6-dichlorophenyl)methoxy]-3-methylphenyl]prop-2-enyl]phenyl]prop-2-enoate
• CAS: 263754-64-9
• 化学式: C₂₇H₂₄Cl₂O₃
• 分子量: 467.392
• InChiKey: FVFJEXQLXCLGPU-IINGMRBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-{(E)-3-[2-(2,6-Dichloro-benzyloxy)-3-methyl-phenyl]-allyl}-phenyl)-acrylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (E)-3-(2-{(E)-3-[2-(2,6-Dichloro-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 (E)-3-(2-{(E)-3-[2-(2,6-Dichloro-benzyloxy)-3-methyl-phenyl]-allyl}-phenyl)-acrylic acid methyl ester
  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

• US6211197B1
  申请人：——

  公开号：US6211197B1

  公开（公告）日：2001-04-03
• Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists
  作者：Michel Belley、Michel Gallant、Bruno Roy、Karine Houde、Nicolas Lachance、Marc Labelle、Laird A. Trimble、Nathalie Chauret、Chun Li、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Gillian M. Greig、Deborah Slipetz、Kathleen M. Metters、Robert Gordon、Chi Chung Chan、Robert J. Zamboni

  DOI：10.1016/j.bmcl.2004.11.051

  日期：2005.2

  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.