N-(benzyloxy)-2-hydroxy-5-stearamidobenzamide | 1585168-77-9

• 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-(benzyloxy)-2-hydroxy-5-stearamidobenzamide
• CAS: 1585168-77-9
• 化学式: C₃₂H₄₈N₂O₄
• 分子量: 524.744
• InChiKey: XLNIRQQVXYSTJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  38.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxy)-2-hydroxy-5-stearamidobenzamide 在 氢气 、 palladium(II) hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 以80%的产率得到N,2-dihydroxy-5-stearamidobenzamide
  参考文献：
  名称：

  Fragment screening reveals salicylic hydroxamic acid as an inhibitor of Trypanosoma brucei GPI GlcNAc-PI de-N-acetylase

  摘要：

  The zinc-metalloenzyme GlcNAc-PI de-N-acetylase is essential for the biosynthesis of mature GPI anchors and has been genetically validated in the bloodstream form of Trypanosoma brucei, which causes African sleeping sickness. We screened a focused library of zinc-binding fragments and identified salicylic hydroxamic acid as a GlcNAc-PI de-N-acetylase inhibitor with high ligand efficiency. This is the first small molecule inhibitor reported for the trypanosome GPI pathway. Investigating the structure activity relationship revealed that hydroxamic acid and 2-OH are essential for potency, and that substitution is tolerated at the 4-and 5-positions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.016
• 作为产物：
  描述：

  5-氨基水杨酸 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 水 、 1,2-二氯乙烷 为溶剂， 反应 83.0h， 生成 N-(benzyloxy)-2-hydroxy-5-stearamidobenzamide
  参考文献：
  名称：

  Fragment screening reveals salicylic hydroxamic acid as an inhibitor of Trypanosoma brucei GPI GlcNAc-PI de-N-acetylase

  摘要：

  The zinc-metalloenzyme GlcNAc-PI de-N-acetylase is essential for the biosynthesis of mature GPI anchors and has been genetically validated in the bloodstream form of Trypanosoma brucei, which causes African sleeping sickness. We screened a focused library of zinc-binding fragments and identified salicylic hydroxamic acid as a GlcNAc-PI de-N-acetylase inhibitor with high ligand efficiency. This is the first small molecule inhibitor reported for the trypanosome GPI pathway. Investigating the structure activity relationship revealed that hydroxamic acid and 2-OH are essential for potency, and that substitution is tolerated at the 4-and 5-positions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.016