ethyl 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(3-methylbenzoyl)piperidine-3-carboxylate | 948589-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(3-methylbenzoyl)piperidine-3-carboxylate
• CAS: 948589-20-6
• 化学式: C₂₇H₃₁NO₆S
• 分子量: 497.612
• InChiKey: HCURQGMFIMCVRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(3-methylbenzoyl)piperidine-3-carboxylate 在 lithium hydroxide 、 盐酸羟胺 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.08h， 生成 3-((4-(but-2-ynyloxy)phenylsulfonyl)methyl)-N-hydroxy-1-(3-methylbenzoyl)piperidine-3-carboxamide
  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 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 ethyl 3-(((4-(but-2-yn-1-yloxy)phenyl)sulfonyl)methyl)-1-(3-methylbenzoyl)piperidine-3-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