{[(N⁶-methyladenin-9-yl)acetyl]imino}diacetic acid | 918334-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {[(N⁶-methyladenin-9-yl)acetyl]imino}diacetic acid
• 英文别名: Glycine, N-(carboxymethyl)-N-[2-[6-(methylamino)-9H-purin-9-yl]acetyl]-；2-[carboxymethyl-[2-[6-(methylamino)purin-9-yl]acetyl]amino]acetic acid
• CAS: 918334-51-7
• 化学式: C₁₂H₁₄N₆O₅
• 分子量: 322.28
• InChiKey: QWMSDMXJTBOCBN-UHFFFAOYSA-N

物化性质

• 沸点：
  718.9±70.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  {[(N⁶-methyladenin-9-yl)acetyl]imino}diacetic acid 、 L-aspartic acid di-tert-butyl ester 、 N,N'-二异丙基碳二亚胺 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 以19.3%的产率得到(2S)-2-[[2-[[2-[[(1S)-1,2-dicarboxyethyl]amino]-2-oxoethyl]-[2-[6-(methylamino)purin-9-yl]acetyl]amino]acetyl]amino]butanedioic acid
  参考文献：
  名称：

  Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase

  摘要：

  Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.

  DOI：

  10.1080/15257770500446857
• 作为产物：
  描述：

  {[(N6-methyladenin-9-yl)acetyl]imino}diacetic acid dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 、 正丁醇 为溶剂， 反应 3.5h， 以78.7%的产率得到{[(N⁶-methyladenin-9-yl)acetyl]imino}diacetic acid
  参考文献：
  名称：

  Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase

  摘要：

  Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.

  DOI：

  10.1080/15257770500446857