methyl (2R)-2-(benzhydrylamino)-3-(3,4-dihydroxyphenyl)propanoate | 626201-05-6

• 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: methyl (2R)-2-(benzhydrylamino)-3-(3,4-dihydroxyphenyl)propanoate
• CAS: 626201-05-6
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: BDWMYTFUNXBQBT-LJQANCHMSA-N

物化性质

• 沸点：
  564.1±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-(benzhydrylamino)-3-(3,4-dihydroxyphenyl)propanoate 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 甲基3-羟基-N-甲基-D-酪氨酸酯
  参考文献：
  名称：

  Design and synthesis of small chemical inhibitors containing different scaffolds for lck SH2 domain

  摘要：

  On the basis of the structure of (R)-rosmarinic acid, a series of small chemical compounds with a different scaffold was synthesized as inhibitors for lck SH2 domain. From ELISA results, most of all chemical compounds showed a similar or a little lower binding activity for lck SH2 domain compared to the lead compound, (R)-rosmarinic acid. It was characterized that the backbone rigidity between two catechol substructures was required for the full activity and acid substructure of the lead compound was important for the activity. We successfully identified novel lead compounds that did not contain phosphotyrosine moiety and might have an improved bioavailability as inhibitor for lck SH2 domain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00735-2
• 作为产物：
  描述：

  methyl N-(diphenylmethylene)-D-3-hydroxytyrosine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 methyl (2R)-2-(benzhydrylamino)-3-(3,4-dihydroxyphenyl)propanoate
  参考文献：
  名称：

  Design and synthesis of small chemical inhibitors containing different scaffolds for lck SH2 domain

  摘要：

  On the basis of the structure of (R)-rosmarinic acid, a series of small chemical compounds with a different scaffold was synthesized as inhibitors for lck SH2 domain. From ELISA results, most of all chemical compounds showed a similar or a little lower binding activity for lck SH2 domain compared to the lead compound, (R)-rosmarinic acid. It was characterized that the backbone rigidity between two catechol substructures was required for the full activity and acid substructure of the lead compound was important for the activity. We successfully identified novel lead compounds that did not contain phosphotyrosine moiety and might have an improved bioavailability as inhibitor for lck SH2 domain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00735-2