N³-cinnamoyl-N³-benzoyloxy-N¹-(tert-butoxycarbonyl)propane diamine | 434343-12-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N³-cinnamoyl-N³-benzoyloxy-N¹-(tert-butoxycarbonyl)propane diamine
• 英文别名: [3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl-[(E)-3-phenylprop-2-enoyl]amino] benzoate
• CAS: 434343-12-1
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: WRJRVUURVIUJGX-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N³-cinnamoyl-N³-benzoyloxy-N¹-(tert-butoxycarbonyl)propane diamine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N³-hydroxyl-N³-cinnamoyl-propane diamine trifluoroacetic acid salt
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Citrate-Based Siderophores as Potential Probes for the Mechanism of Iron Uptake in Mycobacteria

  摘要：

  Several iron chelators containing alpha,beta-unsaturated hydroxamic acid motifs appended to a citric acid platform were synthesized. Mycobacterium paratuberculosis was then challenged to grow in the presence of a panel of siderophores (mycobactin J, deferrioxamine B, acinetoferrin, and nannochelin A) and the new synthetic agents. Of the structures tested, those containing the trans 2-octenoyl motif were preferred over those with trans cinnamoyl groups. In addition, derivatives containing longer tether lengths between the iron binding ligands (C5) were more efficacious and led to higher growth index values. Perhaps most remarkable was the finding that at 2.4 muM a trans 2-octenoylated, citrate-containing imide 6 was nearly 5-fold more effective in stimulating growth than the native chelator, mycobactin J. In this regard, new structural elements were identified (e.g., an imide motif or 2-octenoyl side chain), whose presence stimulated mycobacterial growth.

  DOI：

  10.1021/jm0104522
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 Carbonate buffer 、 TEA 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 N³-cinnamoyl-N³-benzoyloxy-N¹-(tert-butoxycarbonyl)propane diamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Citrate-Based Siderophores as Potential Probes for the Mechanism of Iron Uptake in Mycobacteria

  摘要：

  Several iron chelators containing alpha,beta-unsaturated hydroxamic acid motifs appended to a citric acid platform were synthesized. Mycobacterium paratuberculosis was then challenged to grow in the presence of a panel of siderophores (mycobactin J, deferrioxamine B, acinetoferrin, and nannochelin A) and the new synthetic agents. Of the structures tested, those containing the trans 2-octenoyl motif were preferred over those with trans cinnamoyl groups. In addition, derivatives containing longer tether lengths between the iron binding ligands (C5) were more efficacious and led to higher growth index values. Perhaps most remarkable was the finding that at 2.4 muM a trans 2-octenoylated, citrate-containing imide 6 was nearly 5-fold more effective in stimulating growth than the native chelator, mycobactin J. In this regard, new structural elements were identified (e.g., an imide motif or 2-octenoyl side chain), whose presence stimulated mycobacterial growth.

  DOI：

  10.1021/jm0104522

文献信息

• Synthesis and Biological Evaluation of New Citrate-Based Siderophores as Potential Probes for the Mechanism of Iron Uptake in Mycobacteria
  作者：Hongyan Guo、Saleh A. Naser、George Ghobrial、Phanstiel

  DOI：10.1021/jm0104522

  日期：2002.5.1

  Several iron chelators containing alpha,beta-unsaturated hydroxamic acid motifs appended to a citric acid platform were synthesized. Mycobacterium paratuberculosis was then challenged to grow in the presence of a panel of siderophores (mycobactin J, deferrioxamine B, acinetoferrin, and nannochelin A) and the new synthetic agents. Of the structures tested, those containing the trans 2-octenoyl motif were preferred over those with trans cinnamoyl groups. In addition, derivatives containing longer tether lengths between the iron binding ligands (C5) were more efficacious and led to higher growth index values. Perhaps most remarkable was the finding that at 2.4 muM a trans 2-octenoylated, citrate-containing imide 6 was nearly 5-fold more effective in stimulating growth than the native chelator, mycobactin J. In this regard, new structural elements were identified (e.g., an imide motif or 2-octenoyl side chain), whose presence stimulated mycobacterial growth.