methyl N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate | 1020109-32-3

• 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: methyl N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate
• CAS: 1020109-32-3
• 化学式: C₄₅H₆₀N₆O₁₁
• 分子量: 861.005
• InChiKey: QKLYVRASIYSPPN-BJKOEGOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  62.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  202.22
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine
  参考文献：
  名称：

  Design and synthesis of a siderophore conjugate as a potent PSMA inhibitor and potential diagnostic agent for prostate cancer

  摘要：

  A siderophore conjugate was designed as a potential PSMA inhibitor and diagnostic agent for prostate cancer. A semirigid spacer was incorporated to avoid competitive participation of iron binding by the enzyme inhibitor relative to the siderophore component. Biological test results showed that, even with the extended scaffold, this compound is a potent PSMA inhibitor with an IC50 of 4 nM. This siderophore conjugate may be useful for detection of prostate-derived cancer cells by magnetic resonance imaging (MRI). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.030
• 作为产物：
  描述：

  methyl N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate 、 乙酸酐 在 氢溴酸 、 溶剂黄146 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到methyl N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithinate
  参考文献：
  名称：

  Design and synthesis of a siderophore conjugate as a potent PSMA inhibitor and potential diagnostic agent for prostate cancer

  摘要：

  A siderophore conjugate was designed as a potential PSMA inhibitor and diagnostic agent for prostate cancer. A semirigid spacer was incorporated to avoid competitive participation of iron binding by the enzyme inhibitor relative to the siderophore component. Biological test results showed that, even with the extended scaffold, this compound is a potent PSMA inhibitor with an IC50 of 4 nM. This siderophore conjugate may be useful for detection of prostate-derived cancer cells by magnetic resonance imaging (MRI). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.030