2-(3-ethoxy-3-oxopropyl)-5-(phenoxymethyl)benzoicacid | 1204595-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-ethoxy-3-oxopropyl)-5-(phenoxymethyl)benzoicacid
• CAS: 1204595-15-2
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: MLVLGQQINDSKSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-甲基-1-苯基-2-戊胺 、 2-(3-ethoxy-3-oxopropyl)-5-(phenoxymethyl)benzoicacid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 1: Discovery and exploration of the carboxyamide side chain

  摘要：

  A series of 3-(2-aminocarbonyl-4-phenoxymethylphenyl) propanoic acid analogs were synthesized and evaluated for their EP3 antagonist activity in the presence of additive serum albumin. Several compounds were biologically evaluated for their in vivo efficacy with respect to the PGE(2)-induced uterine contraction in pregnant rats as well as their pharmacokinetics. The discovery process of these potent and selective EP3 antagonists and their structure activity relationship are also presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.023
• 作为产物：
  描述：

  tert-butyl 2-(3-ethoxy-3-oxopropyl)-5-(phenoxymethyl)benzoate 在 三氟乙酸 作用下， 以 苯甲醚 为溶剂， 反应 1.5h， 以88%的产率得到2-(3-ethoxy-3-oxopropyl)-5-(phenoxymethyl)benzoicacid
  参考文献：
  名称：

  3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 1: Discovery and exploration of the carboxyamide side chain

  摘要：

  A series of 3-(2-aminocarbonyl-4-phenoxymethylphenyl) propanoic acid analogs were synthesized and evaluated for their EP3 antagonist activity in the presence of additive serum albumin. Several compounds were biologically evaluated for their in vivo efficacy with respect to the PGE(2)-induced uterine contraction in pregnant rats as well as their pharmacokinetics. The discovery process of these potent and selective EP3 antagonists and their structure activity relationship are also presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.023

文献信息

• 3-(2-Aminocarbonylphenyl)propanoic acid analogs as potent and selective EP3 receptor antagonists. Part 2: Optimization of the side chains to improve in vitro and in vivo potencies
  作者：Masaki Asada、Maki Iwahashi、Tetsuo Obitsu、Atsushi Kinoshita、Yoshihiko Nakai、Takahiro Onoda、Toshihiko Nagase、Motoyuki Tanaka、Yoshiyuki Yamaura、Hiroya Takizawa、Ken Yoshikawa、Kazutoyo Sato、Masami Narita、Shuichi Ohuchida、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2009.12.068

  日期：2010.2

  A series of 3-[2-[(3-methyl-1-phenylbutyl)amino]carbonyl}-4-(phenoxymethyl)phenyl]propanoic acid analogs were synthesized and evaluated for their in vitro potency. In most cases, introduction of one or two substituents into the two phenyl moieties resulted in the tendency of an increase or retention of in vitro activities. Several compounds, which showed excellent subtype selectivity, were evaluated

  合成了一系列3- [2-[（（3-甲基-1-苯基丁基）氨基]羰基} -4-（苯氧基甲基）苯基]丙酸类似物，并评估了其体外效能。在大多数情况下，在两个苯基部分中引入一个或两个取代基导致体外活性增加或保留的趋势。评估了几种具有优异亚型选择性的化合物对妊娠大鼠中PGE 2诱导的子宫收缩的抑制作用，认为这是由EP3受体亚型介导的。还讨论了结构-活性关系（SAR）。