3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(isobutoxycarbonyl)piperidine-3-carboxylic acid | 948589-29-5

• 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: 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(isobutoxycarbonyl)piperidine-3-carboxylic acid
• CAS: 948589-29-5
• 化学式: C₂₂H₂₉NO₇S
• 分子量: 451.541
• InChiKey: VMJDTRJCUAQWIM-UHFFFAOYSA-N

物化性质

• 沸点：
  658.7±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110.21
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(isobutoxycarbonyl)piperidine-3-carboxylic acid 在 盐酸羟胺 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 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 20.0h， 生成 Isobutyl 3-((4-(but-2-ynyloxy)phenylsulfonyl)methyl)-3-(hydroxycarbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Design and synthesis of 3,3-piperidine hydroxamate analogs as selective TACE inhibitors

  摘要：

  Structure-based methods were used to design P-sulfone 3,3-piperidine hydroxamates as TACE inhibitors with the aim of improving selectivity for TACE versus MMP-13. Several compounds in this series were synthesized and evaluated in enzymatic and cell-based assays. These analogs exhibit excellent in vitro potency against isolated TACE enzyme and show good selectivity for TACE over the related metalloproteases MMP-2, -13, and -14. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.022
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 lithium hydroxide 、 TEA 、 potassium carbonate 、 caesium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.08h， 生成 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(isobutoxycarbonyl)piperidine-3-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of 3,3-piperidine hydroxamate analogs as selective TACE inhibitors

  摘要：

  Structure-based methods were used to design P-sulfone 3,3-piperidine hydroxamates as TACE inhibitors with the aim of improving selectivity for TACE versus MMP-13. Several compounds in this series were synthesized and evaluated in enzymatic and cell-based assays. These analogs exhibit excellent in vitro potency against isolated TACE enzyme and show good selectivity for TACE over the related metalloproteases MMP-2, -13, and -14. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.022