(S)-1-(benzylsulfonyl)piperidine-2-carboxylic acid | 251916-58-2

• 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: (S)-1-(benzylsulfonyl)piperidine-2-carboxylic acid
• 英文别名: (2S)-1-benzylsulfonylpiperidine-2-carboxylic acid
• CAS: 251916-58-2
• 化学式: C₁₃H₁₇NO₄S
• 分子量: 283.348
• InChiKey: WTWAHPUUXVQCGB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-三甲氧基苯基)-1-丙醇 、 (S)-1-(benzylsulfonyl)piperidine-2-carboxylic acid 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以21%的产率得到(S)-3-(3,4,5-trimethoxyphenyl)propyl 1-(benzylsulfonyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Pipecolic Acid Derivatives As Small-Molecule Inhibitors of the Legionella MIP Protein

  摘要：

  The macrophage infectivity potentiator (MIP) protein is a major virulence factor of Legionella pneumophila, the causative agent of Legionnaires' disease MIP belongs to the FK506-binding proteins (FKBP) and is necessary for optimal intracellular survival and lung tissue dissemination of L pneumophila We aimed to identify new small-molecule inhibitors of MIP by starting from known FKBP12 ligands Computational analysis, synthesis, and biological testing of pipecolic acid derivatives revealed a promising scaffold for new MIP inhibitors

  DOI：

  10.1021/jm101156y
• 作为产物：
  描述：

  L-哌啶-2-甲酸 在 氯化亚砜 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (S)-1-(benzylsulfonyl)piperidine-2-carboxylic acid
  参考文献：
  名称：

  Pipecolic Acid Derivatives As Small-Molecule Inhibitors of the Legionella MIP Protein

  摘要：

  The macrophage infectivity potentiator (MIP) protein is a major virulence factor of Legionella pneumophila, the causative agent of Legionnaires' disease MIP belongs to the FK506-binding proteins (FKBP) and is necessary for optimal intracellular survival and lung tissue dissemination of L pneumophila We aimed to identify new small-molecule inhibitors of MIP by starting from known FKBP12 ligands Computational analysis, synthesis, and biological testing of pipecolic acid derivatives revealed a promising scaffold for new MIP inhibitors

  DOI：

  10.1021/jm101156y

文献信息

• Inhibiting prolyl isomerase activity by hybrid organic–inorganic molecules containing rhodium(II) fragments
  作者：Jane M. Coughlin、Rituparna Kundu、Julian C. Cooper、Zachary T. Ball

  DOI：10.1016/j.bmcl.2014.09.068

  日期：2014.11

  A small molecule containing a rhodium(II) tetracarboxylate fragment is shown to be a potent inhibitor of the prolyl isomerase FKBP12. The use of small molecules conjugates of rhodium(II) is presented as a general strategy for developing new protein inhibitors based on distinct structural and sequence features of the enzyme active site. (C) 2014 Elsevier Ltd. All rights reserved.