3-(4-((2-phenyloxazol-4-yl)methoxy)phenyl)propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-((2-phenyloxazol-4-yl)methoxy)phenyl)propanoic acid
• 英文别名: 3-{4-[(5-Phenyl-1,3-oxazol-2-yl)methoxy]phenyl}propanoic acid；3-[4-[(5-phenyl-1,3-oxazol-2-yl)methoxy]phenyl]propanoic acid
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: ASGGTPSYLCAVFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-(4-((2-phenyloxazol-4-yl)methoxy)phenyl)propanoate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以0.47 g的产率得到3-(4-((2-phenyloxazol-4-yl)methoxy)phenyl)propanoic acid
  参考文献：
  名称：

  Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40)

  摘要：

  A screening hit that showed a weak (EC50 = 18 mu M), partial agonistic effect on GPR40 was used a prototype for expedited hit expansion effort using a set of advanced building blocks. The latter yielded several 1,3-oxazoles and 1,2,4-oxadiazoles with significantly improved potency (best EC50 = 0.058 mu M). The lead compounds in each chemotype showed a very good ADME profile (aqueous solubility, plasma protein binding, microsomal stability and membrane permeability) and no appreciable inhibition of key cytochromes P450. The compounds reported are significant new starting points for further preclinical development of future diabetic agents with a mechanism of action for which a first-in-class agent is yet to be approved. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.018