2-hydroxyethyl 4-chloro-3-nitrobenzoate | 113658-75-6

• 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: 2-hydroxyethyl 4-chloro-3-nitrobenzoate
• CAS: 113658-75-6
• 化学式: C₉H₈ClNO₅
• 分子量: 245.619
• InChiKey: QFTUKKCZRMFNQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  408.5±35.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 4-chloro-3-nitrobenzoate 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 2-azidoethyl 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
• 作为产物：
  描述：

  乙二醇 、 4-氯-3-硝基苯甲酸 在 氯化亚砜 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 4.0h， 以37%的产率得到2-hydroxyethyl 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

• Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds
  申请人：——

  公开号：US20030055055A1

  公开（公告）日：2003-03-20

  The present invention relates to novel benzimidazole derivatives, pharmaceutical composition containing these compounds, and methods of treatment therewith. The compounds of the invention are useful in the treatment of central nervous system diseases and disorders, which are responsive to modulation of the GABA receptor complex, and in particular for inducing and maintaining anesthesia, sedation and muscle relaxation, as well as for combating febrile convulsions in children. The compounds of the invention may also be used by veterinarians.

  本发明涉及新型苯并咪唑衍生物，含有这些化合物的药物组合物，以及使用这些化合物进行治疗的方法。本发明的化合物在治疗对GABA受体复合物调节敏感的中枢神经系统疾病和紊乱方面具有用途，特别是用于诱导和维持麻醉、镇静和肌肉松弛，以及用于对抗儿童的热性惊厥。本发明的化合物也可以被兽医使用。
• [EN] NOVEL BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE COMPOUNDS<br/>[FR] NOUVEAU DERIVES DE BENZIMIDAZOLE ET COMPOSITIONS PHARMACEUTIQUES COMPRENANT CES COMPOSES
  申请人：NEUROSEARCH AS

  公开号：WO2004089912A1

  公开（公告）日：2004-10-21

  The present invention relates to novel benzimidazole derivatives of the formula (I) as defined in the description and in the claims, pharmaceutical compositions containing these compounds, and methods of treatment therewith. The compounds of the invention are useful in the treatment of central nervous system diseases and disorders, which are responsive to modulation of the GABAA receptor complex, and in particular for inducing and maintaining anaesthesia, sedation and muscle relaxation, as well as for combating febrile convulsions in children. The compounds of the invention may also be used by veterinarians.

  本发明涉及新型苯并咪唑衍生物的公式（I），如描述和索赔中定义的，包含这些化合物的药物组合物，以及使用这些药物进行治疗的方法。本发明的化合物在治疗对GABAA受体复合物调节敏感的中枢神经系统疾病和障碍方面是有用的，特别是用于诱导和维持麻醉、镇静和肌肉松弛，以及对抗儿童的发热性惊厥。本发明的化合物也可被兽医使用。
• BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE COMPOUNDS
  申请人：NEUROSEARCH A/S

  公开号：EP1194410A1

  公开（公告）日：2002-04-10
• NOVEL BENZIMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE COMPOUNDS
  申请人：NEUROSEARCH A/S

  公开号：EP1615896B1

  公开（公告）日：2008-04-23
• EP1615896A1
  申请人：——

  公开号：EP1615896A1

  公开（公告）日：2006-01-18