N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N-[3-(2-(4-methoxycarbonylphenyl)-1,3-dioxolan-2-yl)propyl]amide | 1020109-42-5

• 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: N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N-[3-(2-(4-methoxycarbonylphenyl)-1,3-dioxolan-2-yl)propyl]amide
• CAS: 1020109-42-5
• 化学式: C₅₈H₇₅N₇O₁₄
• 分子量: 1094.27
• InChiKey: DHGKLMFTRAOIPA-QTACXXFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  79.0
• 可旋转键数：
  33.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  249.78
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N-[3-(2-(4-methoxycarbonylphenyl)-1,3-dioxolan-2-yl)propyl]amide 在 甲酸 作用下， 反应 3.0h， 以91%的产率得到N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N-[4-(4-methoxycarbonylphenyl)-4-oxobutyl]amide
  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：

  N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine 、 3-[2-(4-methoxycarbonylphenyl)-1,3-dioxolan-2-yl]propylamine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以89%的产率得到N⁵-acetyl-N⁵-(benzyloxy)-N²-acetyl-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl-N-[3-(2-(4-methoxycarbonylphenyl)-1,3-dioxolan-2-yl)propyl]amide
  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