4-{[6-(methoxycarbonyl)hexyl]amino}-1-(benzyloxy)-2(1H)-pyrimidinone | 189497-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-{[6-(methoxycarbonyl)hexyl]amino}-1-(benzyloxy)-2(1H)-pyrimidinone
• 英文别名: Methyl 7-[(2-oxo-1-phenylmethoxypyrimidin-4-yl)amino]heptanoate
• CAS: 189497-19-6
• 化学式: C₁₉H₂₅N₃O₄
• 分子量: 359.425
• InChiKey: GRSKJQYVWSBBBP-UHFFFAOYSA-N

物化性质

• 沸点：
  477.2±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{[6-(methoxycarbonyl)hexyl]amino}-1-(benzyloxy)-2(1H)-pyrimidinone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以69%的产率得到4-[(6-carboxyhexyl)amino]-1-(benzyloxy)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Novel Iron Sequestering Agents:  Synthesis and Iron-Chelating Properties of Hexadentate Ligands Composed of 1-Hydroxy-2(1H)-pyrimidinone, ω-Amino Carboxylic Acid, and Tris(2-aminoethyl)amine

  摘要：

  Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.

  DOI：

  10.1021/jo961901m
• 作为产物：
  描述：

  N-(苄氧基)脲 在 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 92.0h， 生成 4-{[6-(methoxycarbonyl)hexyl]amino}-1-(benzyloxy)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Novel Iron Sequestering Agents:  Synthesis and Iron-Chelating Properties of Hexadentate Ligands Composed of 1-Hydroxy-2(1H)-pyrimidinone, ω-Amino Carboxylic Acid, and Tris(2-aminoethyl)amine

  摘要：

  Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.

  DOI：

  10.1021/jo961901m

文献信息

• Novel Iron Sequestering Agents:  Synthesis and Iron-Chelating Properties of Hexadentate Ligands Composed of 1-Hydroxy-2(1<i>H</i>)-pyrimidinone, ω-Amino Carboxylic Acid, and Tris(2-aminoethyl)amine
  作者：Junko Ohkanda、Jun Kamitani、Takeshi Tokumitsu、Yoko Hida、Takeo Konakahara、Akira Katoh

  DOI：10.1021/jo961901m

  日期：1997.5.1

  Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.