(2R,S)-amino-2-(1H-tetrazol-5-yl)acetic acid ethyl ester hydrochloride | 1171827-23-8

• 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: (2R,S)-amino-2-(1H-tetrazol-5-yl)acetic acid ethyl ester hydrochloride
• 英文别名: ethyl 2-amino-2-(1H-tetrazol-5-yl)acetate hydrochloride；ethyl 2-amino-2-(2H-tetrazol-5-yl)acetate;hydrochloride
• CAS: 1171827-23-8
• 化学式: C₅H₉N₅O₂*ClH
• 分子量: 207.62
• InChiKey: BXBKCZJGOQMUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 (2R,S)-amino-2-(1H-tetrazol-5-yl)acetic acid ethyl ester hydrochloride 在 吡啶 、 氯甲酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以47%的产率得到ethyl 2-(9Z,12Z)-heptadeca-9,12-dienamido-2-(1H-tetrazol-5-yl)acetate
  参考文献：
  名称：

  Potential Neuroprotective Drugs in Cerebral Ischemia: New Saturated and Polyunsaturated Lipids Coupled to Hydrophilic Moieties: Synthesis and Biological Activity

  摘要：

  The ganglioside GM1 has neuroprotective effects but is not of therapeutic value because of its lack of bioavailability. Thus, molecules that mimic GM I represent a novel approach to neuroprotection. We have synthesized 19 small GM1-like analogues whose simplified structure includes a hydrophobic saturated or unsaturated moiety linked to a hydrophilic moiety. We report their neuroprotective effects in two distinct models of nerve cell death using hippocampus-derived HT22 cells. We found that several analogues protected the HT22 cells from death at concentrations ranging from 2 to 5 mu M. Additional neuroprotective assays using cortical slices injured by glutamate confirmed these results. Since members of the MAP kinase family are known to be key players in nerve cell survival and death, we characterized the role of these kinases in the neuroprotective mechanisms of the GM1-like analogues. Interestingly, the results indicate that the compounds provide neuroprotection through distinct mechanisms of action.

  DOI：

  10.1021/jm900227u
• 作为产物：
  描述：

  ethyl 2-tetrazol-5-yl-2-oximinoacetate 在 Pearlman's catalyst 、 氢气 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以100%的产率得到(2R,S)-amino-2-(1H-tetrazol-5-yl)acetic acid ethyl ester hydrochloride
  参考文献：
  名称：

  Potential Neuroprotective Drugs in Cerebral Ischemia: New Saturated and Polyunsaturated Lipids Coupled to Hydrophilic Moieties: Synthesis and Biological Activity

  摘要：

  The ganglioside GM1 has neuroprotective effects but is not of therapeutic value because of its lack of bioavailability. Thus, molecules that mimic GM I represent a novel approach to neuroprotection. We have synthesized 19 small GM1-like analogues whose simplified structure includes a hydrophobic saturated or unsaturated moiety linked to a hydrophilic moiety. We report their neuroprotective effects in two distinct models of nerve cell death using hippocampus-derived HT22 cells. We found that several analogues protected the HT22 cells from death at concentrations ranging from 2 to 5 mu M. Additional neuroprotective assays using cortical slices injured by glutamate confirmed these results. Since members of the MAP kinase family are known to be key players in nerve cell survival and death, we characterized the role of these kinases in the neuroprotective mechanisms of the GM1-like analogues. Interestingly, the results indicate that the compounds provide neuroprotection through distinct mechanisms of action.

  DOI：

  10.1021/jm900227u

文献信息

• 10.1016/j.ejmech.2024.116642
  作者：Małecki, Piotr H.、Fassauer, Georg M.、Rüger, Nicole、Schulig, Lukas、Link, Andreas、Krylova, Oxana、Heinemann, Udo、Weiss, Manfred S.

  DOI：10.1016/j.ejmech.2024.116642

  日期：——

  understand the binding cavity using an X-ray crystallographic approach to provide a detailed landscape of possible interactions within the under-investigated region of KDM4. Our design strategy was based on utilizing known KDM binding motifs, such as nicotinic acid and tetrazolylhydrazides, as core motifs that we decided to enrich with flexible tails to map the distal histone binding site. The resulting

  KDM4 组蛋白去甲基化酶成为抑制剂开发的令人兴奋的靶标，因为将它们与肿瘤发生直接联系起来的证据越来越多。在这项研究中，我们着手使用 X 射线晶体学方法更好地了解结合腔，以提供 KDM4 研究不足区域内可能相互作用的详细情况。我们的设计策略基于利用已知的 KDM 结合基序（如烟酸和四唑酰肼）作为核心基序，我们决定用柔性尾部富集这些基序以绘制远端组蛋白结合位点。与 KDM4D 结合的新型化合物（KDM4 家族的代表）的 X 射线结构揭示了与组蛋白结合位点远端残基的相互作用模式。配体结合时检测到的最突出的蛋白质重排是阻碍组蛋白结合位点可及性的环运动。除了提供潜在抑制剂可以靶向的新位点外，这些新化合物还可能有助于探索配体在其他 KDM 或 2-氧代戊二酸 （2OG） 依赖性加氧酶的辅因子结合位点远端结合的能力。案例研究证明，鉴于易于获得 X 射线质量晶体，将强大的小结合基序与灵活的尾部相结合以探
• Potential Neuroprotective Drugs in Cerebral Ischemia: New Saturated and Polyunsaturated Lipids Coupled to Hydrophilic Moieties: Synthesis and Biological Activity
  作者：Alain César Biraboneye、Sébastien Madonna、Younes Laras、Slavica Krantic、Pamela Maher、Jean-Louis Kraus

  DOI：10.1021/jm900227u

  日期：2009.7.23

  The ganglioside GM1 has neuroprotective effects but is not of therapeutic value because of its lack of bioavailability. Thus, molecules that mimic GM I represent a novel approach to neuroprotection. We have synthesized 19 small GM1-like analogues whose simplified structure includes a hydrophobic saturated or unsaturated moiety linked to a hydrophilic moiety. We report their neuroprotective effects in two distinct models of nerve cell death using hippocampus-derived HT22 cells. We found that several analogues protected the HT22 cells from death at concentrations ranging from 2 to 5 mu M. Additional neuroprotective assays using cortical slices injured by glutamate confirmed these results. Since members of the MAP kinase family are known to be key players in nerve cell survival and death, we characterized the role of these kinases in the neuroprotective mechanisms of the GM1-like analogues. Interestingly, the results indicate that the compounds provide neuroprotection through distinct mechanisms of action.