3-(3,4-dichlorophenyl)-2-isoxazoline-5-carboxylic acid | 109888-66-6

• 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: 3-(3,4-dichlorophenyl)-2-isoxazoline-5-carboxylic acid
• 英文别名: 3-(3,4-Dichlorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid
• CAS: 109888-66-6
• 化学式: C₁₀H₇Cl₂NO₃
• 分子量: 260.076
• InChiKey: NDHFMONJGUAVQS-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  427.1±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-2-isoxazoline-5-carboxylic acid 、 (S)-N-((3-(3-氟-4-(哌嗪-1-基)苯基)-2-氧代噁唑啉-5-基)甲基)乙酰胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到N-[3-(4-{4-(3-(3,4-dichloro-phenyl)-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl}-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of isoxazolinyl oxazolidinones: Search for potent antibacterial

  摘要：

  A series of (5S) N-(3-{3-fluoro-4-[4-(3-aryl-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl]-phenyl}2-oxo-oxazolidin-5-ylmethyl)-acetamide(6a-o) were synthesized and their in vitro antibacterial activity against various resistant Gram-positive and Gram-negative bacteria were evaluated. Most of the synthesized compounds showed 2 to 10 fold lower MIC values compared to linezolid against Staphylococcus aureus ATCC 25923, ATCC 70069, ATCC 29213, Bacillus cereus MTCC 430, Enterococcus faecalis MTCC439, Klebsiella pneumoniae ATCC 27736, and Streptococcus pyogens. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.133
• 作为产物：
  描述：

  Methyl 3-(3,4-dichlorophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(3,4-dichlorophenyl)-2-isoxazoline-5-carboxylic acid
  参考文献：
  名称：

  [EN] CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  [FR] CERTAINS INHIBITEURS DE KYNURÉNINE-3-MONOOXYGÉNASE, COMPOSITIONS PHARMACEUTIQUES ET PROCÉDÉS D'UTILISATION DE CEUX-CI

  摘要：

  本文提供了某些化学实体。还提供了包括至少一种化学实体和一种或多种药用载体的药物组合物。描述了治疗对KMO活性抑制产生反应的患有某些疾病和疾病的患者的方法，包括向这些患者施用至少一种有效减少疾病或疾病症状的化学实体的数量。这些疾病包括亨廷顿病等神经退行性疾病。还描述了治疗方法，包括单独使用至少一种化学实体或将至少一种化学实体与一种或多种其他治疗剂结合使用。还提供了筛选能够抑制KMO活性的化合物的方法。

  公开号：

  WO2010017132A1

文献信息

• CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  申请人：Wityak John

  公开号：US20120329812A1

  公开（公告）日：2012-12-27

  Certain chemical entities are provided herein. Also provided are pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化学实体。还提供了包含至少一种化学实体和一个或多个药用载体的制药组合物。本文描述了治疗对抑制KMO活性有反应的某些疾病和疾病的患者的方法，包括向这些患者施用至少一种化学实体的有效量以减轻疾病或疾病的症状或迹象。这些疾病包括神经退行性疾病，如亨廷顿病。还描述了治疗方法，包括将至少一种化学实体作为单一活性剂或与一个或多个其他治疗剂联合使用。还提供了筛选抑制KMO活性的化合物的方法。
• US4889551A
  申请人：——

  公开号：US4889551A

  公开（公告）日：1989-12-26
• US4906277A
  申请人：——

  公开号：US4906277A

  公开（公告）日：1990-03-06
• Synthesis and antibacterial evaluation of isoxazolinyl oxazolidinones: Search for potent antibacterial
  作者：Vandana Varshney、Nripendra N. Mishra、Praveen K. Shukla、Devi P. Sahu

  DOI：10.1016/j.bmcl.2009.04.133

  日期：2009.7

  A series of (5S) N-(3-3-fluoro-4-[4-(3-aryl-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl]-phenyl}2-oxo-oxazolidin-5-ylmethyl)-acetamide(6a-o) were synthesized and their in vitro antibacterial activity against various resistant Gram-positive and Gram-negative bacteria were evaluated. Most of the synthesized compounds showed 2 to 10 fold lower MIC values compared to linezolid against Staphylococcus aureus ATCC 25923, ATCC 70069, ATCC 29213, Bacillus cereus MTCC 430, Enterococcus faecalis MTCC439, Klebsiella pneumoniae ATCC 27736, and Streptococcus pyogens. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] CERTAIN KYNURENINE-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] CERTAINS INHIBITEURS DE KYNURÉNINE-3-MONOOXYGÉNASE, COMPOSITIONS PHARMACEUTIQUES ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：CHDI INC

  公开号：WO2010017132A1

  公开（公告）日：2010-02-11

  Certain chemical entities are provided herein. Also provided are pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.

  本文提供了某些化学实体。还提供了包括至少一种化学实体和一种或多种药用载体的药物组合物。描述了治疗对KMO活性抑制产生反应的患有某些疾病和疾病的患者的方法，包括向这些患者施用至少一种有效减少疾病或疾病症状的化学实体的数量。这些疾病包括亨廷顿病等神经退行性疾病。还描述了治疗方法，包括单独使用至少一种化学实体或将至少一种化学实体与一种或多种其他治疗剂结合使用。还提供了筛选能够抑制KMO活性的化合物的方法。