N-(tert-butoxy)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-4-piperidinecarboxamide | 287202-42-0

• 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: N-(tert-butoxy)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-4-piperidinecarboxamide
• 英文别名: 4-[(4-but-2-ynoxyphenyl)sulfonylmethyl]-N-[(2-methylpropan-2-yl)oxy]piperidine-4-carboxamide
• CAS: 287202-42-0
• 化学式: C₂₁H₃₀N₂O₅S
• 分子量: 422.546
• InChiKey: WVHMFZFYUOTLCM-UHFFFAOYSA-N

物化性质

• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxy)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-4-piperidinecarboxamide 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 4-((4-(but-2-ynyloxy)phenylsulfonyl)methyl)-N-hydroxy-1-(pyridin-4-yl)piperidine-4-carboxamide
  参考文献：
  名称：

  Identification of potent and selective TACE inhibitors via the S1 pocket

  摘要：

  By focusing on the P1 portion of the piperidine beta-sulfone ligands we identified a motif that induces selectivity and resulted in a series of TACE inhibitors that demonstrated excellent in vitro potency against isolated TACE enzyme and excellent selectivity over MMPs 1, 2, 9, 13, and 14.

  DOI：

  10.1016/j.bmcl.2006.10.004
• 作为产物：
  描述：

  4-乙基4-(碘甲基)哌啶-1,4-二羧酸-1-叔丁酯 在 甲醇 、 sodium hydroxide 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 caesium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 氘代二甲亚砜 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(tert-butoxy)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}methyl)-4-piperidinecarboxamide
  参考文献：
  名称：

  Identification of potent and selective TACE inhibitors via the S1 pocket

  摘要：

  By focusing on the P1 portion of the piperidine beta-sulfone ligands we identified a motif that induces selectivity and resulted in a series of TACE inhibitors that demonstrated excellent in vitro potency against isolated TACE enzyme and excellent selectivity over MMPs 1, 2, 9, 13, and 14.

  DOI：

  10.1016/j.bmcl.2006.10.004

文献信息

• Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors
  作者：Kaapjoo Park、Alexis Aplasca、Mila T. Du、LinHong Sun、Yi Zhu、Yuhua Zhang、Jeremy I. Levin

  DOI：10.1016/j.bmcl.2006.05.026

  日期：2006.8

  A series of butynyloxyphenyl P-sulfone piperidine hydroxamate TACE inhibitors was designed and synthesized. The resulting structure-activity relationship and MMP selectivity of the series were examined. Of the compounds investigated, 17s has excellent in vitro potency against isolated TACE enzyme, shows good selectivity over MMP-1, -2, -7, -8, -9, -13, and -14, and oral activity in an in vivo mouse model of TNF-alpha production. (c) 2006 Elsevier Ltd. All rights reserved.
• ALKYNYL CONTAINING HYDROXAMIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MATRIX METALLOPROTEINASE (MMP) INHIBITORS / TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS
  申请人：Wyeth Holdings Corporation

  公开号：EP1147085B1

  公开（公告）日：2005-11-16