acetamide deferoxamine | 5722-48-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: acetamide deferoxamine
• 英文别名: desferrioxamine D1；N-Acetyl-desferrioxamin B；N'-[5-[[4-[5-acetamidopentyl(hydroxy)amino]-4-oxobutanoyl]amino]pentyl]-N-[5-[acetyl(hydroxy)amino]pentyl]-N'-hydroxybutanediamide
• CAS: 5722-48-5
• 化学式: C₂₇H₅₀N₆O₉
• 分子量: 602.729
• InChiKey: IEYBTYRDMTXDKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  42
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  209
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  acetamide deferoxamine 生成 [5-[[4-[5-[[4-[5-acetamidopentyl(octanoyloxy)amino]-4-oxobutanoyl]amino]pentyl-octanoyloxyamino]-4-oxobutanoyl]amino]pentyl-acetylamino] octanoate
  参考文献：
  名称：

  GREEN, DONALD E.

  摘要：

  DOI：
• 作为产物：
  描述：

  N(1)-Benzyloxycarbonyl-6,17-dihydroxy-7,10,18-trioxo-6,11,17-triazanonadecylamin 生成 acetamide deferoxamine
  参考文献：
  名称：

  Stoffwechselprodukte von Actinomyceten。36. Mitteilung。黚死SYNTHESE DER铁草胺乙UND d 1

  摘要：

  天然微生物生长因子铁氧嘧啶B和D 1已通过反应顺序ⅢXI合成。

  DOI：

  10.1002/hlca.19620450228

文献信息

• Gorak, Soviet progress in chemistry, 1989, vol. 55, # 11, p. 107 - 109
  作者：Gorak

  DOI：——

  日期：——
• Synthesis and Solution Properties of Deferoxamine Amides
  作者：Peter M. Ihnat、Jonathan L. Vennerstrom、Dennis H. Robinson

  DOI：10.1002/1520-6017(200012)89:12<1525::aid-jps3>3.0.co;2-t

  日期：2000.12

  The poor membrane permeability and oral bioavailability of the iron chelating agent deferoxamine (DFO) mesylate result from the low octanol/water partition coefficient and high aqueous solubility. With the ultimate aim to improve biomembrane permeability while retaining the iron-binding ability of DFO, a series of more lipophilic amides were prepared by reacting the terminal primary amino group with fatty and aromatic acid chlorides or anhydrides. Octanol/water partition coefficients and equilibrium solubilities of these analogs in solvents, chosen to delineate physicochemical interactions, were determined as a function of temperature. Solid-state properties were evaluated by calorimetry. All DFO amide derivatives had higher melting points, indicating that derivatives formed strong intermolecular interactions in the solid phase. Formamidation of the primary amine of deferoxamine resulted in a 200-fold increase in the octanol/water partition coefficient and reduced aqueous solubility at least 2000-fold compared with the parent molecule. The partition coefficient increased and aqueous solubility decreased 2-fold with the addition of each methylene group in the homologous series of aliphatic amides. Solubilities of the derivatives in water-saturated octanol and hexane showed irregular profiles as a function of increasing aliphatic chain length that were attributed to intermolecular packing in the solid state. The temperature dependence of the partition coefficients was interpreted to indicate that interfacial transfer of the deferoxamine amides was, in part, affected by an apparent diminished ability to form energetically favorable interactions in the water-saturated organic phase.
• GORAK, R. D., YKP. XIM. ZH., 55,(1989) N1, S. 1222-1224
  作者：GORAK, R. D.

  DOI：——

  日期：——
• Stoffwechselprodukte von Actinomyceten. 36. Mitteilung. Über die Synthese der Ferrioxamine B und D₁
  作者：V. Prelog、A. Walser

  DOI：10.1002/hlca.19620450228

  日期：——

  The natural microbial growth factors, ferrioxamines B and D1, have been synthesized by the reaction sequence III XI.

  天然微生物生长因子铁氧嘧啶B和D 1已通过反应顺序ⅢXI合成。
• GREEN, DONALD E.
  作者：GREEN, DONALD E.

  DOI：——

  日期：——