[1-[4'-(7-benzyloxycarbamoyl-heptanoylamino)biphenyl-2-ylcarbamoyl]-2-(4-benzyloxy-phenyl)ethyl]carbamic acid tert-butyl ester | 944457-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [1-[4'-(7-benzyloxycarbamoyl-heptanoylamino)biphenyl-2-ylcarbamoyl]-2-(4-benzyloxy-phenyl)ethyl]carbamic acid tert-butyl ester
• CAS: 944457-75-4
• 化学式: C₄₈H₅₄N₄O₇
• 分子量: 798.979
• InChiKey: KFQABSKULNCFFP-QLKFWGTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  144.09
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [1-[4'-(7-benzyloxycarbamoyl-heptanoylamino)biphenyl-2-ylcarbamoyl]-2-(4-benzyloxy-phenyl)ethyl]carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74.1%的产率得到octanedioic acid {2'-[2-amino-3-(4-benzyloxyphenyl)propionylamino]biphenyl-4-yl}amide benzyloxyamide
  参考文献：
  名称：

  Functional Differences in Epigenetic ModulatorsSuperiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies

  摘要：

  We compare the ability of two structurally different classes of epigenetic modulators, namely, histone deacetylase (HDAC) inhibitors containing either a hydroxamate or a mercaptoacetamide as the zinc binding group, to protect cortical neurons in culture from oxidative stress-induced death. This study reveals that some of the mercaptoacetamide-based HDAC inhibitors are fully protective, whereas the hydroxamates show toxicity at higher concentrations. Our present results appear to be consistent with the possibility that the mercaptoacetamide-based HDAC inhibitors interact with a different subset of the HDAC isozymes [less activity at HDAC1 and 2 correlates with less inhibitor toxicity], or alternatively, are interacting selectively with only the cytoplasmic HDACs that are crucial for protection from oxidative stress.

  DOI：

  10.1021/jm070178x
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 在 吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [1-[4'-(7-benzyloxycarbamoyl-heptanoylamino)biphenyl-2-ylcarbamoyl]-2-(4-benzyloxy-phenyl)ethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Functional Differences in Epigenetic ModulatorsSuperiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies

  摘要：

  We compare the ability of two structurally different classes of epigenetic modulators, namely, histone deacetylase (HDAC) inhibitors containing either a hydroxamate or a mercaptoacetamide as the zinc binding group, to protect cortical neurons in culture from oxidative stress-induced death. This study reveals that some of the mercaptoacetamide-based HDAC inhibitors are fully protective, whereas the hydroxamates show toxicity at higher concentrations. Our present results appear to be consistent with the possibility that the mercaptoacetamide-based HDAC inhibitors interact with a different subset of the HDAC isozymes [less activity at HDAC1 and 2 correlates with less inhibitor toxicity], or alternatively, are interacting selectively with only the cytoplasmic HDACs that are crucial for protection from oxidative stress.

  DOI：

  10.1021/jm070178x