N¹,N⁵-(N⁴-hydroxy,N⁴-cinnamoyl-4'-aminobutyl)-3-tert-butoxycarbonyl-1,5-citric diamide | 434343-22-3

• 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: N¹,N⁵-(N⁴-hydroxy,N⁴-cinnamoyl-4'-aminobutyl)-3-tert-butoxycarbonyl-1,5-citric diamide
• 英文别名: tert-butyl 2-hydroxy-4-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-[2-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-oxoethyl]-4-oxobutanoate
• CAS: 434343-22-3
• 化学式: C₃₆H₄₈N₄O₉
• 分子量: 680.799
• InChiKey: HLRBFOHTYYTQQQ-FRCMOREXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  49
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N¹,N⁵-(N⁴-hydroxy,N⁴-cinnamoyl-4'-aminobutyl)-3-tert-butoxycarbonyl-1,5-citric diamide 在 三氟乙酸 作用下， 反应 2.0h， 以84%的产率得到2-hydroxy-4-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-[2-[4-[hydroxy-[(E)-3-phenylprop-2-enoyl]amino]butylamino]-2-oxoethyl]-4-oxobutanoic acid
  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：

  N⁴-cinnamoyl-N⁴-benzoyloxy-N¹-(tert-butoxycarbonyl)butane diamine 在 ammonium hydroxide 、 TEA 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 N¹,N⁵-(N⁴-hydroxy,N⁴-cinnamoyl-4'-aminobutyl)-3-tert-butoxycarbonyl-1,5-citric diamide
  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