prop-2-yn-1-yl 4-chloro-3-nitrobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: prop-2-yn-1-yl 4-chloro-3-nitrobenzoate
• 英文别名: Prop-2-ynyl 4-chloro-3-nitrobenzoate；prop-2-ynyl 4-chloro-3-nitrobenzoate
• 化学式: C₁₀H₆ClNO₄
• 分子量: 239.615
• InChiKey: WSGNVBSLVBLGGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  prop-2-yn-1-yl 4-chloro-3-nitrobenzoate 、 环己胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  [EN] COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS
  [FR] COMPOSÉS, COMPOSITIONS ET MÉTHODES DE MODULATION DE LA FERROPTOSE ET DE TRAITEMENT DE TROUBLES EXCITOTOXIQUES

  摘要：

  本公开提供一种具有结构（1）的化合物。还提供了含有药用可接受载体和根据本公开披露的一个或多个化合物的组合物。此外，还提供了治疗或改善受体内兴奋毒性紊乱影响的方法，调节受体内铁死亡的方法，减少细胞内活性氧（ROS）的方法，治疗或改善神经退行性疾病影响的方法，缓解正在接受放射治疗和/或免疫治疗的受体的副作用的方法，以及治疗或改善与受体内铁死亡相关的感染影响的方法。

  公开号：

  WO2020113028A1
• 作为产物：
  描述：

  2-丙炔-1-醇 、 4-氯-3-硝基苯甲酸 在 氯化亚砜 作用下， 反应 18.0h， 以96%的产率得到prop-2-yn-1-yl 4-chloro-3-nitrobenzoate
  参考文献：
  名称：

  Synthesis of a Suite of Bioorthogonal Glutathione S-Transferase Substrates and Their Enzymatic Incorporation for Protein Immobilization

  摘要：

  Label-free protein immobilization allows precise detection of biomolecular events. Preserving enzyme function is intrinsically challenging for these strategies. Considering that glutathione S-transferase (GST) is a broadly employed enzymatic fusion tag, we reported a label-free self-catalyzed immobilization for Schistosoma japonicum GST. We now report the synthesis, structure, and enzymology of a set of 20 smSNAREs (small molecule SNAr-electrophiles). These smSNAREs mimic (electronically) the canonical GST substrate 1-chloro-2,4-dinitrobenzene (CDNB), and bear a wide variety of bioorthogonal functionalities such as alkynes, aldehydes, acetals, and azides. Sixteen analogues including the chloro- and nitro substituted 1, 3, 5, 6, 7, 11, 12, and 13 participated in the GST-catalyzed conjugation, indicating the substrate tolerance of the enzymatic H-site of SjGST. Using UV-vis spectroscopy, we estimate the efficiency of conjugation as a function of substrate diversity. Using LC-MS, we characterized the conjugates formed under each enzymatic transformation. Significant deviations from the canonical CDNB architecture are tolerated. Relative rates between nitro and chloro substituents indicate the nucleophilic addition step is rate determining. Enzyme immobilization on glass slides is affected by additional surface interactions and therefore does not reflect kinetic profiles observed in solution. This new class of heterobifunctional linkers enables a single-step and uniform protein capture on designer surfaces.

  DOI：

  10.1021/jo401278x

文献信息

• Synthesis of a Suite of Bioorthogonal Glutathione S-Transferase Substrates and Their Enzymatic Incorporation for Protein Immobilization
  作者：Alden E. Voelker、Rajesh Viswanathan

  DOI：10.1021/jo401278x

  日期：2013.10.4

  Label-free protein immobilization allows precise detection of biomolecular events. Preserving enzyme function is intrinsically challenging for these strategies. Considering that glutathione S-transferase (GST) is a broadly employed enzymatic fusion tag, we reported a label-free self-catalyzed immobilization for Schistosoma japonicum GST. We now report the synthesis, structure, and enzymology of a set of 20 smSNAREs (small molecule SNAr-electrophiles). These smSNAREs mimic (electronically) the canonical GST substrate 1-chloro-2,4-dinitrobenzene (CDNB), and bear a wide variety of bioorthogonal functionalities such as alkynes, aldehydes, acetals, and azides. Sixteen analogues including the chloro- and nitro substituted 1, 3, 5, 6, 7, 11, 12, and 13 participated in the GST-catalyzed conjugation, indicating the substrate tolerance of the enzymatic H-site of SjGST. Using UV-vis spectroscopy, we estimate the efficiency of conjugation as a function of substrate diversity. Using LC-MS, we characterized the conjugates formed under each enzymatic transformation. Significant deviations from the canonical CDNB architecture are tolerated. Relative rates between nitro and chloro substituents indicate the nucleophilic addition step is rate determining. Enzyme immobilization on glass slides is affected by additional surface interactions and therefore does not reflect kinetic profiles observed in solution. This new class of heterobifunctional linkers enables a single-step and uniform protein capture on designer surfaces.
• [EN] COMPOUNDS, COMPOSITIONS, AND METHODS FOR MODULATING FERROPTOSIS AND TREATING EXCITOTOXIC DISORDERS<br/>[FR] COMPOSÉS, COMPOSITIONS ET MÉTHODES DE MODULATION DE LA FERROPTOSE ET DE TRAITEMENT DE TROUBLES EXCITOTOXIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2020113028A1

  公开（公告）日：2020-06-04

  The present disclosure provides, inter alia, a compound having the structure (1). Also provided are compositions containing a pharmaceutically acceptable carrier and one or more compounds according to the present disclosure. Further provided are methods for treating or ameliorating the effects of an excitotoxic disorder in a subject, methods of modulating ferroptosis in a subject, methods of reducing reactive oxygen species (ROS) in a cell, methods for treating or ameliorating the effects of a neurodegenerative disease, methods for alleviating side effects in a subject undergoing radiotherapy and/or immunotherapy, and methods for treating or ameliorating the effects of an infection associated with ferroptosis in a subject.

  本公开提供一种具有结构（1）的化合物。还提供了含有药用可接受载体和根据本公开披露的一个或多个化合物的组合物。此外，还提供了治疗或改善受体内兴奋毒性紊乱影响的方法，调节受体内铁死亡的方法，减少细胞内活性氧（ROS）的方法，治疗或改善神经退行性疾病影响的方法，缓解正在接受放射治疗和/或免疫治疗的受体的副作用的方法，以及治疗或改善与受体内铁死亡相关的感染影响的方法。