N-(4-(ethylthio)phenyl)-6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-amine | 1054579-45-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-(ethylthio)phenyl)-6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-amine
• 英文别名: N-(4-ethylsulfanylphenyl)-5-nitro-6-[4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]pyrimidin-4-amine
• CAS: 1054579-45-1
• 化学式: C₂₂H₂₇N₇O₃S
• 分子量: 469.567
• InChiKey: YFLIBDGYNPRMAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-(1-(6-氯-5-硝基嘧啶-4-基)哌啶-4-基)-3-异丙基-1,2,4-恶二唑 、 4-(乙硫基)苯胺 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.08h， 以55%的产率得到N-(4-(ethylthio)phenyl)-6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  Discovery of the First Potent and Orally Efficacious Agonist of the Orphan G-Protein Coupled Receptor 119

  摘要：

  GPR119 is a rhodopsin-like GPCR expressed in pancreatic beta-cells and incretin releasing cells in the GI tract. As with incretins, GPR119 increase,; cAMP levels in these cell types. thus making it a highly attractive potential target for the treatment of diabetes. The discovery of the first reported potent agonist of GPR119, 2-fluoro-4-methanesulfonyl-phenyl)-{6-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-5-nitro-pyrimidin-4-yl}-amine (8g, AR231453), is described starting from an initial inverse agonist screening hit. Compound 8g showed in vivo activity in rodents and was active in an oral glucose tolerance test in mice following oral administration.

  DOI：

  10.1021/jm8006867

文献信息

• Discovery of the First Potent and Orally Efficacious Agonist of the Orphan G-Protein Coupled Receptor 119
  作者：Graeme Semple、Beatriz Fioravanti、Guillherme Pereira、Imelda Calderon、Jane Uy、Karoline Choi、Yifeng Xiong、Albert Ren、Michael Morgan、Vibha Dave、William Thomsen、David J. Unett、Charles Xing、Stuart Bossie、Chris Carroll、Zhi-Liang Chu、Andrew J. Grottick、Erin K. Hauser、James Leonard、Robert M. Jones

  DOI：10.1021/jm8006867

  日期：2008.9.11

  GPR119 is a rhodopsin-like GPCR expressed in pancreatic beta-cells and incretin releasing cells in the GI tract. As with incretins, GPR119 increase,; cAMP levels in these cell types. thus making it a highly attractive potential target for the treatment of diabetes. The discovery of the first reported potent agonist of GPR119, 2-fluoro-4-methanesulfonyl-phenyl)-6-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-5-nitro-pyrimidin-4-yl}-amine (8g, AR231453), is described starting from an initial inverse agonist screening hit. Compound 8g showed in vivo activity in rodents and was active in an oral glucose tolerance test in mice following oral administration.