[(R)-2-((R)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]carbamic acid tertbutyl ester | 1415969-16-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(R)-2-((R)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]carbamic acid tertbutyl ester
• CAS: 1415969-16-2
• 化学式: C₁₅H₂₃N₃O₃
• 分子量: 293.366
• InChiKey: RHYZSLLOKCTWLC-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  82.43
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(R)-2-((R)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]carbamic acid tertbutyl ester 以 2,2,2-三氟乙醇 为溶剂， 反应 3.0h， 以86%的产率得到(R)-1-((R)-2-amino-2-cyclopropyl-acetyl)-pyrrolidine-3-carbonitrile
  参考文献：
  名称：

  3-Amido Pyrrolopyrazine JAK Kinase Inhibitors: Development of a JAK3 vs JAK1 Selective Inhibitor and Evaluation in Cellular and in Vivo Models

  摘要：

  The Janus kinases (JAKs) are involved in multiple signaling networks relevant to inflammatory diseases, and inhibition of one or more members of this class may modulate disease activity or progression. We optimized a new inhibitor scaffold, 3-amido-5-cyclopropylpyrrolopyrazines, to a potent example with reasonable kinome selectivity, including selectivity for JAK3 versus JAK1, and good biopharmaceutical properties. Evaluation of this analogue in cellular and in vivo models confirmed functional selectivity for modulation of a JAK3/JAK1-dependent IL-2 stimulated pathway over a JAK1/JAK2/Tyk2-dependent IL-6 stimulated pathway.

  DOI：

  10.1021/jm301646k
• 作为产物：
  描述：

  (R)-吡咯烷-3-甲腈盐酸盐 、 (R)-2-((tert-butoxycarbonyl)amino)-2-cyclopropylacetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以59%的产率得到[(R)-2-((R)-3-cyano-pyrrolidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]carbamic acid tertbutyl ester
  参考文献：
  名称：

  3-Amido Pyrrolopyrazine JAK Kinase Inhibitors: Development of a JAK3 vs JAK1 Selective Inhibitor and Evaluation in Cellular and in Vivo Models

  摘要：

  The Janus kinases (JAKs) are involved in multiple signaling networks relevant to inflammatory diseases, and inhibition of one or more members of this class may modulate disease activity or progression. We optimized a new inhibitor scaffold, 3-amido-5-cyclopropylpyrrolopyrazines, to a potent example with reasonable kinome selectivity, including selectivity for JAK3 versus JAK1, and good biopharmaceutical properties. Evaluation of this analogue in cellular and in vivo models confirmed functional selectivity for modulation of a JAK3/JAK1-dependent IL-2 stimulated pathway over a JAK1/JAK2/Tyk2-dependent IL-6 stimulated pathway.

  DOI：

  10.1021/jm301646k