diethyl 2-[4-({(3S,5S,6R)-2-oxo-5,6-diphenyl-4-[benzyloxycarbonyl]morpholin-3-yl}methyl)phenyl]-2-hydroxypropane-1,3-dioate | 863719-48-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: diethyl 2-[4-({(3S,5S,6R)-2-oxo-5,6-diphenyl-4-[benzyloxycarbonyl]morpholin-3-yl}methyl)phenyl]-2-hydroxypropane-1,3-dioate
• 英文别名: diethyl 2-hydroxy-2-[4-[[(3S,5S,6R)-2-oxo-5,6-diphenyl-4-phenylmethoxycarbonylmorpholin-3-yl]methyl]phenyl]propanedioate
• CAS: 863719-48-6
• 化学式: C₃₈H₃₇NO₉
• 分子量: 651.713
• InChiKey: JTJVGJPEWJXHGF-XFCANUNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 2-[4-({(3S,5S,6R)-2-oxo-5,6-diphenyl-4-[benzyloxycarbonyl]morpholin-3-yl}methyl)phenyl]-2-hydroxypropane-1,3-dioate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides

  摘要：

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.

  DOI：

  10.1021/jm050154v
• 作为产物：
  描述：

  酮基丙二酸二乙酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四氯化锡 作用下， 以 四氯化碳 为溶剂， 反应 19.0h， 生成 diethyl 2-[4-({(3S,5S,6R)-2-oxo-5,6-diphenyl-4-[benzyloxycarbonyl]morpholin-3-yl}methyl)phenyl]-2-hydroxypropane-1,3-dioate
  参考文献：
  名称：

  Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides

  摘要：

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.

  DOI：

  10.1021/jm050154v

文献信息

• Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides
  作者：Sang-Uk Kang、Karen M. Worthy、Lakshman K. Bindu、Manchao Zhang、Dajun Yang、Robert J. Fisher、Terrence R. Burke

  DOI：10.1021/jm050154v

  日期：2005.8.1

  A new phosphotyrosyl mimetic 4-(alpha-hydroxymalonyl)phenylalanine and its incorporation into a Grb2 SH2 domain-binding tripeptide are presented. In whole-cell studies using malonyl ethyl ester prodrug derivatives, it was observed that the 4-(alpha-hydroxymalonyl)phenylalanyl-containing peptide exhibited greater efficacy than the nonhydroxylated 4-(malonyl)phenylalanyl-containing congener in blocking the association of Grb2 with activated erbB-2 tyrosine kinase. These results are consistent with de-esterification and at least partial intracellular decarboxylation.