3',5'-di-tert-butyltyrosine benzyl ester | 500695-43-2

• 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: 3',5'-di-tert-butyltyrosine benzyl ester
• 英文别名: benzyl 2-amino-3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate
• CAS: 500695-43-2
• 化学式: C₂₄H₃₃NO₃
• 分子量: 383.531
• InChiKey: VBPSEZFCVXWYEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3',5'-di-tert-butyltyrosine benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 6.0h， 生成 (3S,8aS)-3-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  Synthesis and Biological Activity of Novel Neuroprotective Diketopiperazines

  摘要：

  The cyclic dipeptide cyclo[His-Pro] (CHP) is synthesized endogenously de novo and as a breakdown product of thyrotropin-releasing hormone (TRH). a tripeptide with known neuroprotective activity. We synthesized two isomeric compounds based on the structure of CHP, in which the histidine residue was replaced by 3.5-di-tert-butyltyrosine (DBT), a phenolic amino acid that traps reactive oxygen species. These novel diketopiperazines prevented neuronal death in an in vitro model of traumatic injury. In addition, they dose-dependent prevented death caused by the direct induction of free radicals, and by calcium mobilization through an agent that evokes rapid. necrotic death. The drugs showed activity in the latter system at picomolar concentrations. The neuroprotective profile of these compounds suggests that they may be useful as treatments for neuronal degeneration in potentially through several different mechanisms. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00132-3
• 作为产物：
  描述：

  2,6-二叔丁基-4-溴甲基苯酚 、 N-二苯亚甲基甘氨酸苄酯 在 lithium hexamethyldisilazane 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.25h， 以54%的产率得到3',5'-di-tert-butyltyrosine benzyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of Novel Neuroprotective Diketopiperazines

  摘要：

  The cyclic dipeptide cyclo[His-Pro] (CHP) is synthesized endogenously de novo and as a breakdown product of thyrotropin-releasing hormone (TRH). a tripeptide with known neuroprotective activity. We synthesized two isomeric compounds based on the structure of CHP, in which the histidine residue was replaced by 3.5-di-tert-butyltyrosine (DBT), a phenolic amino acid that traps reactive oxygen species. These novel diketopiperazines prevented neuronal death in an in vitro model of traumatic injury. In addition, they dose-dependent prevented death caused by the direct induction of free radicals, and by calcium mobilization through an agent that evokes rapid. necrotic death. The drugs showed activity in the latter system at picomolar concentrations. The neuroprotective profile of these compounds suggests that they may be useful as treatments for neuronal degeneration in potentially through several different mechanisms. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00132-3