7-chloro-4-hydroxy-3-(3-nitrophenyl)quinolin-2(1H)-one | 142326-43-0

• 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
• 英文名称: 7-chloro-4-hydroxy-3-(3-nitrophenyl)quinolin-2(1H)-one
• 英文别名: 7-chloro-4-hydroxy-3-(3-nitrophenyl)-2(1H)-quinolone；7-chloro-4-hydroxy-3-(3-nitrophenyl)-1H-quinolin-2-one
• CAS: 142326-43-0
• 化学式: C₁₅H₉ClN₂O₄
• 分子量: 316.7
• InChiKey: ZGWFFDAPDOFKMH-UHFFFAOYSA-N

物化性质

• 熔点：
  >310 °C
• 沸点：
  567.1±50.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-4-hydroxy-3-(3-nitrophenyl)quinolin-2(1H)-one 在 盐酸 、 titanium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到3-(3-aminophenyl)-7-chloro-4-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  Evaluation and Biological Properties of Reactive Ligands for the Mapping of the Glycine Site on the N-Methyl-d-aspartate (NMDA) Receptor

  摘要：

  The glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor, given its potential as pharmacological target, has been thoroughly studied by structure-activity relationships, which has made possible its description in terms of spatial limits and interactions of various types. A structural model, based on mutational analysis and sequence alignements, has been proposed. Yet, the amino acid residues responsible for the interactions with the ligand have not been unambiguously characterized. To evidence nucleophilic pocket-lining residues, we have designed and synthesized reactive glycine-site ligands derived from 3-substituted 4-hydroxy-quinolin-2(1H)-ones by introducing various electrophilic groups at different positions of the molecule. These ligands were found to have high affinity at the glycine site and to be functional antagonists by inhibiting glycine/glutamate-induced currents in transfected oocytes. The correlation between their potency and their substitution pattern was strictly consistent with previously established structure-activity relationships. Most ligands displayed intrinsic reactivity toward cysteine, but none inactivated wild-type receptors. This is consistent with the model since it indicates the absence of exposed cysteine in the glycine-binding site. A strategy of cysteine incorporation by point mutations at selected polypeptide positions will create unambiguously localized targets for our reactive probes.

  DOI：

  10.1021/jm9910730

文献信息

• Hydroxyquinolone derivatives
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0481676A1

  公开（公告）日：1992-04-22

  A class of 4-hydroxy-2-(1 H)-quinolone derivatives, substituted at the 3-position by an optionally substituted aryl substituent, are selective non-competitive antagonists of NMDA receptors and/or are antagonists of AMPA receptors, and are therefore of utility in the treatment of conditions, such as neurodegenerative disorders, convulsions or schizophrenia, which require the administration of an NMDA and/or AMPA receptor antagonist.

  一类 4-羟基-2-(1H)-喹诺酮衍生物在 3 位被任选取代的芳基取代基取代，是 NMDA 受体的选择性非竞争性拮抗剂和/或 AMPA 受体的拮抗剂，因此可用于治疗神经退行性疾病、惊厥或精神分裂症等需要施用 NMDA 和/或 AMPA 受体拮抗剂的疾病。
• US5348962A
  申请人：——

  公开号：US5348962A

  公开（公告）日：1994-09-20
• US5559125A
  申请人：——

  公开号：US5559125A

  公开（公告）日：1996-09-24