N-(2-furanylmethyl)-5-methyl-2-phenyl-4-oxazolemethanamine | 866613-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-furanylmethyl)-5-methyl-2-phenyl-4-oxazolemethanamine
• 英文别名: 1-(furan-2-yl)-N-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]methanamine
• CAS: 866613-46-9
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: SPGWGQTZWVSZIV-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±55.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-formyl-2,6-dimethylphenoxy)-2-methylpropanoate 、 N-(2-furanylmethyl)-5-methyl-2-phenyl-4-oxazolemethanamine 在 sodium triacetoxyborohydride 作用下， 以 二氯甲烷 为溶剂， 生成 Ethyl 2-[4-[[furan-2-ylmethyl-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoate
  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
• 作为产物：
  描述：

  糠醛 、 (5-甲基-2-苯基-1,3-噁唑-4-基)甲胺 在 sodium tetrahydroborate 作用下， 以 乙醇-D1 为溶剂， 生成 N-(2-furanylmethyl)-5-methyl-2-phenyl-4-oxazolemethanamine
  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