2-[4-[[Furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid | 1415228-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-[[Furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid
• 英文别名: 2-[4-[[furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid
• CAS: 1415228-39-5
• 化学式: C₂₈H₃₀N₂O₆
• 分子量: 490.556
• InChiKey: DAVWDSNIJIBJLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Ethyl 2-[4-[[furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-[4-[[Furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2-methoxyphenoxy]-2-methylpropanoic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of novel zwitterionic compounds as PPARα/γ dual agonists (1)

  摘要：

  We describe here the design, syntheses and structure-activity relationships (SAR) of novel zwitterionic compounds as non-thiazolidinedion (TZD) based peroxisome proliferator activated receptor (PPAR) alpha/gamma dual agonists. We commenced the medicinal research with compound 1 originated by Eli Lilly, which was reported to possess PPAR alpha/gamma dual agonist activity. We incorporated an amine linker and optimized it on the nitrogen of the linker, thereby envisioning the enhancement of the PPAR alpha/gamma dual agonist activity together with altering the physicochemical properties. As a result, we could generate compounds showing the PPAR alpha/gamma dual activity, especially among which compound 22e had a franylmethyl group on the linker and 2,6-dimethyl phenyl ring at the carboxylic acid head group furnishing a highly potent dual agonist activity, together with a great glucose lowering effect. Moreover, it remedied the lipid profile, that is, triglyceride without body weight gain in the db/db mice model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.092

文献信息

• Design, synthesis and evaluation of novel zwitterionic compounds as PPARα/γ dual agonists (1)
  作者：Yoshihiro Shibata、Katsuji Kagechika、Mitsuhiro Yamaguchi、Hideo Kubo、Hiroyuki Usui

  DOI：10.1016/j.bmcl.2012.09.092

  日期：2012.12

  We describe here the design, syntheses and structure-activity relationships (SAR) of novel zwitterionic compounds as non-thiazolidinedion (TZD) based peroxisome proliferator activated receptor (PPAR) alpha/gamma dual agonists. We commenced the medicinal research with compound 1 originated by Eli Lilly, which was reported to possess PPAR alpha/gamma dual agonist activity. We incorporated an amine linker and optimized it on the nitrogen of the linker, thereby envisioning the enhancement of the PPAR alpha/gamma dual agonist activity together with altering the physicochemical properties. As a result, we could generate compounds showing the PPAR alpha/gamma dual activity, especially among which compound 22e had a franylmethyl group on the linker and 2,6-dimethyl phenyl ring at the carboxylic acid head group furnishing a highly potent dual agonist activity, together with a great glucose lowering effect. Moreover, it remedied the lipid profile, that is, triglyceride without body weight gain in the db/db mice model. (C) 2012 Elsevier Ltd. All rights reserved.