(1S,2S,5S)-N-hydroxy-5-(2-oxo-2-(piperidin-1-yl)ethyl)-2-(4-phenylpiperazine-1-carbonyl)cyclohexanecarboxamide | 1176144-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1S,2S,5S)-N-hydroxy-5-(2-oxo-2-(piperidin-1-yl)ethyl)-2-(4-phenylpiperazine-1-carbonyl)cyclohexanecarboxamide
• 英文别名: (1S,2S,5S)-N-hydroxy-5-(2-oxo-2-piperidin-1-ylethyl)-2-(4-phenylpiperazine-1-carbonyl)cyclohexane-1-carboxamide
• CAS: 1176144-96-9
• 化学式: C₂₅H₃₆N₄O₄
• 分子量: 456.585
• InChiKey: SPGSQKKTHWOODB-BVSLBCMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(2-oxo-2-piperidin-1-yl-ethyl)-2-(S)-(4-phenyl-piperazine-1-carbonyl)-cyclohexan-(S)-carboxylic acid benzyloxy-amide 在 5% Pd-BaSO4 、 氢气 作用下， 生成 (1S,2S,5R)-N-hydroxy-5-(2-oxo-2-piperidin-1-ylethyl)-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxamide 、 (1S,2S,5S)-N-hydroxy-5-(2-oxo-2-(piperidin-1-yl)ethyl)-2-(4-phenylpiperazine-1-carbonyl)cyclohexanecarboxamide
  参考文献：
  名称：

  Compelling P1 substituent affect on metalloprotease binding profile enables the design of a novel cyclohexyl core scaffold with excellent MMP selectivity and HER-2 sheddase inhibition

  摘要：

  A serendipitous discovery that the metalloprotease binding pro. le of a novel class of 2-carboxamide-3-hydroxamic acid piperidines could be significantly attenuated by the modi. cation of the unexplored P1 substituent enabled the design and synthesis of a novel 2-carboxamide-1-hydroxamic acid cyclohexyl scaffold core that exhibited excellent HER-2 potency and unprecedented MMP-selectivity that we believe would not have been possible via conventional P1' perturbations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.143