5,7-二氯-3-羟基喹啉-2(1h)-酮 | 176170-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5,7-二氯-3-羟基喹啉-2(1h)-酮
• 英文名称: 5,7-dichloro-3-hydroxyquinolin-2(1H)-one
• 英文别名: 5,7-dichloro-3-hydroxy-1H-quinolin-2-one
• CAS: 176170-12-0
• 化学式: C₉H₅Cl₂NO₂
• 分子量: 230.05
• InChiKey: BYQGONOAAITQHT-UHFFFAOYSA-N

物化性质

• 沸点：
  456.2±45.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  5,7-二氯-3-羟基喹啉-2(1h)-酮 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5,7-trichloro-3-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5
• 作为产物：
  描述：

  4,6-二氯靛红 在 盐酸 、 sodium hydroxide 、 二乙胺 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 5,7-二氯-3-羟基喹啉-2(1h)-酮
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5

文献信息

• US5597922A
  申请人：——

  公开号：US5597922A

  公开（公告）日：1997-01-28
• [EN] GLYCINE RECEPTOR ANTAGONIST PHARMACOPHORE<br/>[FR] PHARMACOPHORE D'ANTAGONISTES DU RECEPTEUR DE LA GLYCINE
  申请人：STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of THE OREGON HEALTH SCIENCES UNIVERSITY AND THE UNIVERSITY OF OREGON, EUGENE OREGON

  公开号：WO1996004288A1

  公开（公告）日：1996-02-15

  (EN) Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotropic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.(FR) L'invention se rapporte à des procédés de traitement ou de prévention de la perte neuronale associée à l'attaque, à l'ischémie, aux traumatismes du SNC (système nerveux central), à l'hypoglycémie et aux interventions chirurgicales, ainsi qu'au traitement des maladies dégénératives telles que la maladie d'Alzheimer, la sclérose latérale amyotrophique, la maladie de Huntington et le syndrome de Down, et au traitement ou à la prévention des conséquences fâcheuses de l'hyperactivité des acides aminés excitateurs, et au traitement de l'anxiété, de la douleur chronique, des convulsions et à l'induction d'une anesthésie. Ces procédés consistent à administrer à un animal nécessitant ce type de traitement un composé qui se lie fortement au récepteur de la glycine.
• 3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor
  作者：Sing-Yuen Sit、Frederick J. Ehrgott、Jinnian Gao、Nicholas A. Meanwell

  DOI：10.1016/0960-894x(96)00031-5

  日期：1996.3

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.