N-(tert-Butoxycarbonyl)-3,5-di-tert-butyl-4-hydroxyphenylalanine

• 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: N-(tert-Butoxycarbonyl)-3,5-di-tert-butyl-4-hydroxyphenylalanine
• 英文别名: 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• 化学式: C₂₂H₃₅NO₅
• 分子量: 393.524
• InChiKey: UCUUYYPQQJMSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-3,5-di-tert-butyl-4-hydroxyphenylalanine 在 1-羟基苯并三唑 、 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 为溶剂， 反应 4.0h， 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 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 、 叔丁醇 为溶剂， 反应 10.25h， 生成 N-(tert-Butoxycarbonyl)-3,5-di-tert-butyl-4-hydroxyphenylalanine
  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

文献信息

• Synthesis and Biological Activity of Novel Neuroprotective Diketopiperazines
  作者：K.R.C Prakash、Y Tang、Alan P Kozikowski、Judith L Flippen-Anderson、Susan M Knoblach、Alan I Faden

  DOI：10.1016/s0968-0896(02)00132-3

  日期：2002.9

  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.