1-(2-((trimethylsilyl)oxy)ethyl)piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-((trimethylsilyl)oxy)ethyl)piperazine
• 化学式: C₉H₂₂N₂OSi
• 分子量: 202.372
• InChiKey: KOEIYJAZANHLKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.5
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2-((trimethylsilyl)oxy)ethyl)piperazine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 [3-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl] acetate
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008
• 作为产物：
  描述：

  N-羟乙基哌嗪 、 三甲基氯硅烷 以 甲苯 为溶剂， 反应 3.0h， 生成 1-(2-((trimethylsilyl)oxy)ethyl)piperazine
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008

文献信息

• [EN] ARBIDOL ANALOGS WITH IMPROVED INFLUENZA HEMAGGLUTININ POTENCY<br/>[FR] ANALOGUES D'ARBIDOL AYANT UNE PUISSANCE AMÉLIORÉE VIS-À-VIS DE L'HÉMAGGLUTININE D'INFLUENZA
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2018112128A1

  公开（公告）日：2018-06-21

  The invention provides a series of analogs of arbidol having enhanced binding activity with respect to influenza hemagglutinin. Accordingly, the invention can provide a method of inhibiting the bioactivity of viral hemagglutinin activity, which is an essential step in the entry of infectious viral particles into host cells. The invention also can provide a method of treatment of influence, comprising administering an effective amount of a compound of formula (A), wherein X is S or O, to a patient afflicted therewith.

  这项发明提供了一系列与阿比多尔类似物，其在与流感血凝素结合活性方面具有增强的效果。因此，该发明可以提供一种抑制病毒血凝素生物活性的方法，这是感染性病毒颗粒进入宿主细胞的关键步骤。该发明还可以提供一种治疗流感的方法，包括向患者施用化合物(A)的有效剂量，其中X为S或O。
• Structure-based optimization and synthesis of antiviral drug Arbidol analogues with significantly improved affinity to influenza hemagglutinin
  作者：Zoë V.F. Wright、Nicholas C. Wu、Rameshwar U. Kadam、Ian A. Wilson、Dennis W. Wolan

  DOI：10.1016/j.bmcl.2017.06.074

  日期：2017.8

  of a meta-hydroxy group to the thiophenol moiety of Arbidol to replace a structured water molecule in the binding pocket resulted in a dramatic increase in affinity against both H3 (1150-fold) and H1 (98-fold) hemagglutinin subtypes. Our analogues represent novel leads to yield more potent compounds against hemagglutinin that block viral entry.

  流感是一种高度传染性的呼吸道病毒感染，仅在美国每年就造成50,000例死亡。对具有新颖作用方式的新疗法的需求至关重要。我们确定了带有流感血凝素的Arbidol的X射线结构，发现它位于明显的结合口袋中。在本文中，我们报告了基于共配合物与生物层干涉法相结合的结构-活性关系研究，以评估我们化合物的结合。加元-Arbidol的硫酚部分的羟基取代了结合口袋中的结构化水分子，导致对H3（1150倍）和H1（98倍）血凝素亚型的亲和力显着增加。我们的类似物代表了新颖的线索，可产生更强大的抗血凝素化合物，从而阻止病毒进入。