1-(Benzyloxy)-3-(carboxyethyl)-5,6-dimethyl-2(1H)-pyrazinone | 162610-61-9

• 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: 1-(Benzyloxy)-3-(carboxyethyl)-5,6-dimethyl-2(1H)-pyrazinone
• 英文别名: N-benzyloxy-3-carboxyethyl-5,6-dimethyl-2(1H)-pyrazinone；1-benzyloxy-3-carboxyethyl-5,6-dimethyl-2(1H)pyrazinone；3-(5,6-Dimethyl-3-oxo-4-phenylmethoxypyrazin-2-yl)propanoic acid
• CAS: 162610-61-9
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: KXQQLXVJJWFKFE-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Benzyloxy)-3-(carboxyethyl)-5,6-dimethyl-2(1H)-pyrazinone 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-<3-<1-(Benzyloxy)-5,6-dimethyl-2-oxo-1,2-dihydropyraz-3-yl>propanoyl>-L-leucine
  参考文献：
  名称：

  N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine

  摘要：

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.

  DOI：

  10.1021/jo00111a015
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-甲酯 在 盐酸 、 sodium hydroxide 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.75h， 生成 1-(Benzyloxy)-3-(carboxyethyl)-5,6-dimethyl-2(1H)-pyrazinone
  参考文献：
  名称：

  N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine

  摘要：

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.

  DOI：

  10.1021/jo00111a015

文献信息

• N-Hydroxyamide-Containing Heterocycles. Part 5.1 Synthesis of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-pyrazinone, Aliphatic Diamine, and 1,1,1-Tris(carboxyethoxymethyl)ethane, and Properties of Their Ferric Complexes
  作者：Junko Ohkanda、Akira Katoh

  DOI：10.1016/0040-4020(95)00839-z

  日期：1995.11

  N-hydroxy-2(1H)-pyrazinone connected to tricarboxylic acid by an aliphatic diamine through amide bonds were synthesized. UV-vis spectra of the 1:1 molar mixtures of 3HOPRnCMe and ferric ion in aqueous solution and the mole ratio plot strongly supported the formation of intramolecular 1:1 ferne complexes. The relative stability constants (log K 20.6–21.7) of the complexes were affected by the spacer length in a molecule

  合成了含有N-羟基-2（1 H）-吡嗪酮的新型六齿配体（3HOPR n CMe），该N-羟基-2（1 H）-吡嗪酮通过脂族二胺通过酰胺键与三羧酸连接。水溶液中3HOPR n CMe和三价铁离子的1：1摩尔混合物的UV-vis光谱和摩尔比图强烈支持分子内1：1蕨类化合物的形成。配合物的相对稳定性常数（log K 20.6–21.7）受分子中间隔基长度的影响。此外，3HOPR n CMe与天然铁载体去铁胺B相比，对人转铁蛋白的除铁效率更高。
• The Influence of the Chirality of Synthetic Iron Chelators Bearing<i>N</i>-Hydroxy-2(1<i>H</i>)-pyrazinones and Amino Acid Residues upon Iron Removal from Human Transferrin
  作者：Junko Ohkanda、Akira Katoh

  DOI：10.1246/cl.1996.423

  日期：1996.6

  New chiral iron chelators bearing N-hydroxy-2(1H)-pyrazinone, D-amino acid residues, and tris(2-aminoethyl)amine were synthesized, and their kinetic behavior of iron removal from human transferrin was investigated. The rate of iron removal by the chelator bearing D-alanine residue was suppressed to only one fourth that of L-alanine derivative.

  合成了带有 N-羟基-2(1H)-吡嗪酮、D-氨基酸残基和三 (2-氨基乙基) 胺的新型手性铁螯合剂，并研究了它们从人转铁蛋白中去除铁的动力学行为。带有 D-丙氨酸残基的螯合剂去除铁的速率被抑制到只有 L-丙氨酸衍生物的四分之一。
• N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine
  作者：Junko Ohkanda、Akira Katoh

  DOI：10.1021/jo00111a015

  日期：1995.3

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.