N,N',N''-(次氮三-2,1-乙二基)三(3-羟基-2-氧代-1(2H)-吡啶乙酰胺 | 99110-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N,N',N''-(次氮三-2,1-乙二基)三(3-羟基-2-氧代-1(2H)-吡啶乙酰胺
• 英文名称: N,N,N-tris<2-(3-hydroxy-2-oxo-1,2-dihydropyridin-1-yl)acetamido>ethylamine
• 英文别名: N,N-di-[2-(3-hydroxy-2-oxopyrid-1-ylacetamido)ethyl]-2-(3-hydroxy-2-oxopyrid-1-ylacetamido)-ethylamine；N-[2-[bis[2-[[2-(3-hydroxy-2-oxopyridin-1-yl)acetyl]amino]ethyl]amino]ethyl]-2-(3-hydroxy-2-oxopyridin-1-yl)acetamide
• CAS: 99110-76-6
• 化学式: C₂₇H₃₃N₇O₉
• 分子量: 599.601
• InChiKey: QNZKJNRJNNXADJ-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C (decomp)
• 沸点：
  1137.8±65.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  212
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1-carboxymethyl-3-hydroxy-2(1H)pyridinone 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 N,N',N''-(次氮三-2,1-乙二基)三(3-羟基-2-氧代-1(2H)-吡啶乙酰胺
  参考文献：
  名称：

  Synthetic Studies into 3-Hydroxy-2(1)-pyridinone Based Hexadentate Metal(III) Ion Chelators

  摘要：

  An improved synthesis and purification of the hexadentate chelators, N,N,N,-tris[2-(3-hydroxy-2-oxo-1,2-dihydropyridin-1-yl)acetamido]ethylamine, 8a and N,N,N,-tris[2-(3-hydroxy-4-methyl-2-oxo-1,2-dihydropyridin-1-yl)acetamido]ethylamine, 8b is described.

  DOI：

  10.1080/00397919808006860

文献信息

• Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties and biological activity
  作者：Michael Streater、Paul D. Taylor、Robert C. Hider、John Porter

  DOI：10.1021/jm00168a033

  日期：1990.6

  The synthesis of a range of novel bidentate and hexadentate ligands containing the chelating moiety 3-hydroxy-2(1H)-pyridinone is described. The pKa values of the ligands and the stability constants of their iron(III) complexes have been determined. The stability constant of the iron(III) complex of one of the hexadentate ligands is comparable to that of desferrioxamine B. The distribution coefficients

  描述了一系列包含螯合部分3-羟基-2（1H）-吡啶酮的新颖的二齿和六齿配体的合成。已经确定了配体的pKa值及其铁（III）配合物的稳定性常数。六齿配体之一的铁（III）配合物的稳定性常数与去铁胺B相当。配体及其铁（III）配合物的分布系数也被确定。新型六齿化合物之一已显示出可显着增强肝细胞和铁超载小鼠的铁（III）排泄。
• Synthesis, physico-chemical and iron(III)-chelating properties of novel hexadentate 3-hydroxy-2(1H)pyridinone ligands
  作者：Bijaya L Rai、Hicham Khodr、Robert C Hider

  DOI：10.1016/s0040-4020(98)01091-6

  日期：1999.1

  Synthesis of hexadentate ligands via the in situ formation of 1-hydroxy benzotriazolyl active ester in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, TBTU as a coupling agent is described. The pKa values and distribution coefficient values (1-octanol/water) of the ligands and the stability constants of their iron(III) complexes are reported.

  六齿配位体的合成通过在原位在2-（1的存在形成1-羟基苯并三唑活性酯的ħ苯并三唑-1-基）-1,1,3,3-四甲基脲四氟硼酸盐，TBTU作为偶联剂是描述。报道了配体的pKa值和分布系数值（1-辛醇/水）及其铁（III）配合物的稳定性常数。
• Hydroxypyridone derivatives and pharmaceutical compositions containing them
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0138421A2

  公开（公告）日：1985-04-24

  Compounds in which two or more rings, being a 3-hydroxpy- pyrid-2-one, 3-hydroxypyrid-4-one or 1-hydroxpyrid-2-one, are linked are of value in the treatment of patients having a toxic concentration of a metal, particularly iron, in the body whilst the iron complexes of such compounds are of value in the treatment of iron deficiency anaemia.

  两个或两个以上环（3-羟基吡啶-2-酮、3-羟基吡啶-4-酮或 1-羟基吡啶-2-酮）相连的化合物对治疗体内金属（尤其是铁）浓度过高的病人很有价值，而此类化合物的铁络合物对治疗缺铁性贫血症很有价值。
• Pharmaceutical compositions
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：EP0357150A1

  公开（公告）日：1990-03-07

  Iron complexes of a compound in which 2 or more rings, being a 3-hydroxypyrid-2-one, 3-hydroxypyrid-4- one or 1-hydroxypyrid-2-one, are linked have value in the treatment of iron deficiency anaemia.

  2 个或 2 个以上环（3-羟基吡啶-2-酮、3-羟基吡啶-4-酮或 1-羟基吡啶-2-酮）相连的化合物的铁络合物具有治疗缺铁性贫血症的价值。
• STREATER, MICHAEL;TAYLOR, PAUL D.;HIDER, ROBERT C.;PORTER, JOHN, J. MED. CHEM., 33,(1990) N, C. 1749-1755
  作者：STREATER, MICHAEL、TAYLOR, PAUL D.、HIDER, ROBERT C.、PORTER, JOHN

  DOI：——

  日期：——