1-(tert-butyl) 3-ethyl 3-(azidomethyl)piperidine-1,3-dicarboxylate | 1314131-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(tert-butyl) 3-ethyl 3-(azidomethyl)piperidine-1,3-dicarboxylate
• CAS: 1314131-39-9
• 化学式: C₁₄H₂₄N₄O₄
• 分子量: 312.369
• InChiKey: NBYPSNMQJRWYPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  104.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyl) 3-ethyl 3-(azidomethyl)piperidine-1,3-dicarboxylate 在 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 以97%的产率得到1-(tert-butyl) 3-ethyl 3-(aminomethyl)piperidine-1,3-dicarboxylate
  参考文献：
  名称：

  Discovery of selective and orally available spiro-3-piperidyl ATP-competitive MK2 inhibitors

  摘要：

  The identification of a potent, selective, and orally available MK2 inhibitor series is described. The initial absence of oral bioavailability was successfully tackled by moving the basic nitrogen of the spiro-4-piperidyl moiety towards the electron-deficient pyrrolepyridinedione core, thereby reducing the pK(a) and improving Caco-2 permeability. The resulting racemic spiro-3-piperidyl analogues were separated by chiral preparative HPLC, and the activity towards MK2 inhibition was shown to reside mostly in the first eluting stereoisomer. This led to the identification of new MK2 inhibitors, such as (S)-23, with low nanomolar biochemical inhibition (EC(50) 7.4 nM) and submicromolar cellular target engagement activity (EC(50) 0.5 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.016
• 作为产物：
  描述：

  1-(tert-butyl) 3-ethyl 3-(iodomethyl)piperidine-1,3-dicarboxylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以69%的产率得到1-(tert-butyl) 3-ethyl 3-(azidomethyl)piperidine-1,3-dicarboxylate
  参考文献：
  名称：

  Discovery of selective and orally available spiro-3-piperidyl ATP-competitive MK2 inhibitors

  摘要：

  The identification of a potent, selective, and orally available MK2 inhibitor series is described. The initial absence of oral bioavailability was successfully tackled by moving the basic nitrogen of the spiro-4-piperidyl moiety towards the electron-deficient pyrrolepyridinedione core, thereby reducing the pK(a) and improving Caco-2 permeability. The resulting racemic spiro-3-piperidyl analogues were separated by chiral preparative HPLC, and the activity towards MK2 inhibition was shown to reside mostly in the first eluting stereoisomer. This led to the identification of new MK2 inhibitors, such as (S)-23, with low nanomolar biochemical inhibition (EC(50) 7.4 nM) and submicromolar cellular target engagement activity (EC(50) 0.5 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.016