tert-butyl 4-(5-(2-methylpyridin-3-yloxy)-6-(3-methylureido)pyridin-3-ylthio)piperidine-1-carboxylate | 1442669-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 4-(5-(2-methylpyridin-3-yloxy)-6-(3-methylureido)pyridin-3-ylthio)piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-[6-(methylcarbamoylamino)-5-(2-methylpyridin-3-yl)oxypyridin-3-yl]sulfanylpiperidine-1-carboxylate；tert-butyl 4-[6-(methylcarbamoylamino)-5-(2-methylpyridin-3-yl)oxypyridin-3-yl]sulfanylpiperidine-1-carboxylate
• CAS: 1442669-48-8
• 化学式: C₂₃H₃₁N₅O₄S
• 分子量: 473.596
• InChiKey: GWPGRDSUKXWFFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(5-(2-methylpyridin-3-yloxy)-6-(3-methylureido)pyridin-3-ylthio)piperidine-1-carboxylate 、 甲基磺酰氯 在 三氟乙酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 生成 1-Methyl-3-[3-(2-methylpyridin-3-yl)oxy-5-(1-methylsulfonylpiperidin-4-yl)sulfanylpyridin-2-yl]urea
  参考文献：
  名称：

  Discovery of 2-Pyridylureas as Glucokinase Activators

  摘要：

  Glucokinase (GK) is the rate-limiting step for insulin release from the pancreas in response to high levels of glucose. Flux through GK also contributes to reducing hepatic glucose outpout. Since many individuals with type 2 diabetes appear to have an inadequacy or defect in one or both of these processes, identifying compounds that can allosterically activate GK may address this issue. Herein we report the identification and initial optimization of a novel series of glucokinase activators (GKAs). Optimization led to the identification of 33 as compound that displayed activity in an oral glucose tolerance test (OGTT) in normal and diabetic mice.

  DOI：

  10.1021/jm501204z
• 作为产物：
  描述：

  5-溴-2-氰基-3-硝基吡啶 在 吡啶 、 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 tert-butyl 4-(5-(2-methylpyridin-3-yloxy)-6-(3-methylureido)pyridin-3-ylthio)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery of 2-Pyridylureas as Glucokinase Activators

  摘要：

  Glucokinase (GK) is the rate-limiting step for insulin release from the pancreas in response to high levels of glucose. Flux through GK also contributes to reducing hepatic glucose outpout. Since many individuals with type 2 diabetes appear to have an inadequacy or defect in one or both of these processes, identifying compounds that can allosterically activate GK may address this issue. Herein we report the identification and initial optimization of a novel series of glucokinase activators (GKAs). Optimization led to the identification of 33 as compound that displayed activity in an oral glucose tolerance test (OGTT) in normal and diabetic mice.

  DOI：

  10.1021/jm501204z