N-(3-azidopropyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxamide | 1112977-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-azidopropyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxamide
• CAS: 1112977-83-9
• 化学式: C₁₁H₁₆N₄O₃
• 分子量: 252.273
• InChiKey: MEBIHBKMLAPZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  104.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3-azidopropyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxamide 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到DAz-1
  参考文献：
  名称：

  Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins

  摘要：

  We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modi. cations in the cell-cycle regulatory phosphatase Cdc25A. In addition, we show that DAz-1 has superior potency in cells compared to a biotinylated derivative. Collectively, these. findings set the stage for the development of activity-based inhibitors of Cdc25 cell-cycle phosphatases, which are sensitive to the redox state of the active-site cysteine and demonstrate the advantage of bioorthogonal conjugation methods to detect protein sulfenic acids in cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.073
• 作为产物：
  描述：

  3-methoxy-5-oxo-cyclohex-3-ene-1-carboxylic acid 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-(3-azidopropyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxamide
  参考文献：
  名称：

  Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins

  摘要：

  We have developed an improved synthesis for the cell-permeable, sulfenic acid probe DAz-1. Using DAz-1, we detect sulfenic acid modi. cations in the cell-cycle regulatory phosphatase Cdc25A. In addition, we show that DAz-1 has superior potency in cells compared to a biotinylated derivative. Collectively, these. findings set the stage for the development of activity-based inhibitors of Cdc25 cell-cycle phosphatases, which are sensitive to the redox state of the active-site cysteine and demonstrate the advantage of bioorthogonal conjugation methods to detect protein sulfenic acids in cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.073