(2S)-1-(3-acetamido-4-hydroxy-2-oxobutanoyl)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide | 1207757-67-2

• 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: (2S)-1-(3-acetamido-4-hydroxy-2-oxobutanoyl)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide
• CAS: 1207757-67-2
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: UAESRVZIIAKLAV-ANYOKISRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1-(3-acetamido-4-hydroxy-2-oxobutanoyl)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide 在 二苄基二乙基胺基膦 、 5-(乙硫基)-1H-四唑 、 叔丁基过氧化氢 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 癸烷 、 甲醇 为溶剂， -40.0~20.0 ℃ 、101.33 kPa 条件下， 反应 16.83h， 以5 mg的产率得到
  参考文献：
  名称：

  Convergent Synthesis of α-Ketoamide Inhibitors of Pin1

  摘要：

  A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl2 to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC50 values of 100 and 200 mu W were surprisingly weak for Pin1 peptidyl prolyl isomerase.

  DOI：

  10.1021/ol9027013
• 作为产物：
  描述：

  (2S)-1-(3-acetamido-2-oxo-4-phenylmethoxybutanoyl)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide 在 三氯化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以65%的产率得到(2S)-1-(3-acetamido-4-hydroxy-2-oxobutanoyl)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Convergent Synthesis of α-Ketoamide Inhibitors of Pin1

  摘要：

  A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl2 to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC50 values of 100 and 200 mu W were surprisingly weak for Pin1 peptidyl prolyl isomerase.

  DOI：

  10.1021/ol9027013

文献信息

• Convergent Synthesis of α-Ketoamide Inhibitors of Pin1
  作者：Guoyan G. Xu、Felicia A. Etzkorn

  DOI：10.1021/ol9027013

  日期：2010.2.19

  A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl2 to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC50 values of 100 and 200 mu W were surprisingly weak for Pin1 peptidyl prolyl isomerase.