methyl 3-{4-[(4-bromobenzyl)oxy]phenyl}propanoate | 866587-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 3-{4-[(4-bromobenzyl)oxy]phenyl}propanoate
• 英文别名: Methyl 3-[4-[(4-bromophenyl)methoxy]phenyl]propanoate
• CAS: 866587-92-0
• 化学式: C₁₇H₁₇BrO₃
• 分子量: 349.224
• InChiKey: SSVMLCICTJABTL-UHFFFAOYSA-N

物化性质

• 沸点：
  437.9±30.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  methyl 3-{4-[(4-bromobenzyl)oxy]phenyl}propanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-{4-[(4-Bromobenzyl)oxy]phenyl}propanoic acid
  参考文献：
  名称：

  Structure−Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469

  摘要：

  The free fatty acid 1 receptor (FFA1 or GPR40), which is highly expressed on pancreatic beta-cells and amplifies glucose-stimulated insulin secretion, has emerged as attractive target for the treatment of type 2 diabetes Several FFA1 agonists containing the para-substituted dihydrocinnamic acid moiety are known. We here present a structure-activity relationship study of this compound family suggesting that the central methyleneoxy linker is preferable for the smaller compounds whereas the central methyleneamine linker gives higher potency to the larger compounds. The study resulted in the discovery of the potent and selective full FFA1 agonist TUG-469 (29).

  DOI：

  10.1021/ml100106c
• 作为产物：
  描述：

  对羟基苯丙酸甲酯 、 对溴溴苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 methyl 3-{4-[(4-bromobenzyl)oxy]phenyl}propanoate
  参考文献：
  名称：

  Structure−Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469

  摘要：

  The free fatty acid 1 receptor (FFA1 or GPR40), which is highly expressed on pancreatic beta-cells and amplifies glucose-stimulated insulin secretion, has emerged as attractive target for the treatment of type 2 diabetes Several FFA1 agonists containing the para-substituted dihydrocinnamic acid moiety are known. We here present a structure-activity relationship study of this compound family suggesting that the central methyleneoxy linker is preferable for the smaller compounds whereas the central methyleneamine linker gives higher potency to the larger compounds. The study resulted in the discovery of the potent and selective full FFA1 agonist TUG-469 (29).

  DOI：

  10.1021/ml100106c

文献信息

• Alkoxyphenylpropanoic Acid Derivatives
  申请人：Yasuma Tsuneo

  公开号：US20070213364A1

  公开（公告）日：2007-09-13

  The present invention aims at provision of a novel compound having a GPR40 receptor function modulating action, which is useful as an insulin secretagogue, an agent for the prophylaxis or treatment of diabetes and the like. The compound represented by the formula: wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonistic activity and superior properties as pharmaceutical products such as stability and the like, and can be safe and useful pharmaceutical agents as agents for the prophylaxis or treatment of GPR40 receptor-related pathology or diseases in mammals.

  本发明旨在提供一种新型化合物，具有GPR40受体功能调节作用，可用作胰岛素分泌剂，用于预防或治疗糖尿病等药物。本发明的化合物由以下式表示：其中每个符号如描述中所定义，其盐和其前药，意外地具有优越的GPR40受体激动活性和优越的药物特性，如稳定性等，并且可以作为安全和有用的药物代理剂，用于哺乳动物的GPR40受体相关病理或疾病的预防或治疗。
• Alkoxyphenylpropanoic acid derivatives
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2253315A1

  公开（公告）日：2010-11-24

  The present invention aims at provision of a novel compound having a GPR40 receptor function modulating action, which is useful as an insulin secretagogue, an agent for the prophylaxis or treatment of diabetes and the like. The compound represented by the formula: wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonistic activity and superior properties as pharmaceutical products such as stability and the like, and can be safe and useful pharmaceutical agents as agents for the prophylaxis or treatment of GPR40 receptor-related pathology or diseases in mammals.

  本发明旨在提供一种新型化合物，该化合物具有调节 GPR40 受体功能的作用，可用作胰岛素分泌剂、预防或治疗糖尿病的药物等。该化合物由式表示： 其中各符号如描述中所定义的本发明的化合物、其盐及其原药出乎意料地具有优异的 GPR40 受体激动活性和作为药剂产品的优异特性，如稳定性等，可作为预防或治疗哺乳动物 GPR40 受体相关病理或疾病的药剂，是安全有用的药剂。
• ALKOXYPHENYLPROPANOIC ACID DERIVATIVES
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1731505B1

  公开（公告）日：2015-01-14
• US7517910B2
  申请人：——

  公开号：US7517910B2

  公开（公告）日：2009-04-14
• Structure−Activity Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist TUG-469
  作者：Elisabeth Christiansen、Maria E. Due-Hansen、Christian Urban、Nicole Merten、Michael Pfleiderer、Kasper K. Karlsen、Sanne S. Rasmussen、Mette Steensgaard、Alexandra Hamacher、Johannes Schmidt、Christel Drewke、Rasmus Koefoed Petersen、Karsten Kristiansen、Susanne Ullrich、Evi Kostenis、Matthias U. Kassack、Trond Ulven

  DOI：10.1021/ml100106c

  日期：2010.10.14

  The free fatty acid 1 receptor (FFA1 or GPR40), which is highly expressed on pancreatic beta-cells and amplifies glucose-stimulated insulin secretion, has emerged as attractive target for the treatment of type 2 diabetes Several FFA1 agonists containing the para-substituted dihydrocinnamic acid moiety are known. We here present a structure-activity relationship study of this compound family suggesting that the central methyleneoxy linker is preferable for the smaller compounds whereas the central methyleneamine linker gives higher potency to the larger compounds. The study resulted in the discovery of the potent and selective full FFA1 agonist TUG-469 (29).