3-ethoxy-3-{4-[(3-methylbenzyl)oxy]phenyl}propanoic acid | 1610979-29-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-ethoxy-3-{4-[(3-methylbenzyl)oxy]phenyl}propanoic acid
• 英文别名: 3-Ethoxy-3-[4-[(3-methylphenyl)methoxy]phenyl]propanoic acid；3-ethoxy-3-[4-[(3-methylphenyl)methoxy]phenyl]propanoic acid
• CAS: 1610979-29-7
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: PMWLRBOJRSICTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-hydroxypropionate 在 四丁基氟化铵 、 三苯基膦 、 sodium hydroxide 、 silver(l) oxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 3-ethoxy-3-{4-[(3-methylbenzyl)oxy]phenyl}propanoic acid
  参考文献：
  名称：

  Optimization of 3-aryl-3-ethoxypropanoic acids and discovery of the potent GPR40 agonist DS-1558

  摘要：

  GPR40 agonists stimulate insulin secretion only under the presence of high glucose concentration. Based on this mechanism, GPR40 agonists are believed to be promising novel insulin secretagogues with low risk of hypoglycemia. The optimizations of 3-aryl-3-ethoxypropanoic acids were performed to improve in vitro activity. We discovered compound 29r (DS-1558), (3S)-3-ethoxy-3-(4-{[(1R)-4-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]oxy}phenyl)propanoic acid, which was confirmed to have an enhancing effect on glucose-dependent insulin secretion after intravenous glucose injection in SD rats. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.028

文献信息

• Optimization of 3-aryl-3-ethoxypropanoic acids and discovery of the potent GPR40 agonist DS-1558
  作者：Rieko Takano、Masao Yoshida、Masahiro Inoue、Takeshi Honda、Ryutaro Nakashima、Koji Matsumoto、Tatsuya Yano、Tsuneaki Ogata、Nobuaki Watanabe、Masakazu Hirouchi、Takako Kimura、Narihiro Toda

  DOI：10.1016/j.bmc.2015.07.028

  日期：2015.9

  GPR40 agonists stimulate insulin secretion only under the presence of high glucose concentration. Based on this mechanism, GPR40 agonists are believed to be promising novel insulin secretagogues with low risk of hypoglycemia. The optimizations of 3-aryl-3-ethoxypropanoic acids were performed to improve in vitro activity. We discovered compound 29r (DS-1558), (3S)-3-ethoxy-3-(4-[(1R)-4-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]oxy}phenyl)propanoic acid, which was confirmed to have an enhancing effect on glucose-dependent insulin secretion after intravenous glucose injection in SD rats. (C) 2015 Elsevier Ltd. All rights reserved.