5-((3,5-dichlorophenylamino)methyl)-1H-pyrazol-3(2H)-one | 1227692-79-6

• 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: 5-((3,5-dichlorophenylamino)methyl)-1H-pyrazol-3(2H)-one
• 英文别名: 5-[(3,5-dichloroanilino)methyl]-1,2-dihydropyrazol-3-one
• CAS: 1227692-79-6
• 化学式: C₁₀H₉Cl₂N₃O
• 分子量: 258.107
• InChiKey: CGMGCTWXFWSVPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 4-(N-(3,5-dichlorophenyl)phenylsulfonamido)-3-oxobutanoate 在 氢溴酸 、 溶剂黄146 、 肼 、 对羟基苯甲酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 5-((3,5-dichlorophenylamino)methyl)-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  Arylazanylpyrazolone Derivatives as Inhibitors of Mutant Superoxide Dismutase 1 Dependent Protein Aggregation for the Treatment of Amyotrophic Lateral Sclerosis

  摘要：

  The arylsulfanylpyrazolone and aryloxanylpyrazolone scaffolds previously were reported to inhibit Cu/Zn superoxide dismutase 1 dependent protein aggregation and to extend survival in the ALS mouse model. However, further evaluation of these compounds indicated weak pharmacokinetic properties and a relatively low maximum tolerated dose. On the basis of an ADME analysis, a new series of compounds, the arylazanylpyrazolones, has been synthesized, and structure-activity relationships were determined. The SAR results showed that the pyrazolone ring is critical to cellular protection. The NMR, IR, and computational analyses suggest that phenol-type tautomers of the pyrazolone ring are the active pharmacophore with the arylazanylpyrazolone analogues. A comparison of experimental and calculated IR spectra is shown to be a valuable method to identify the predominant tautomer.

  DOI：

  10.1021/jm400079a

文献信息

• TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS
  申请人：Kirsch Donald R.

  公开号：US20110237907A1

  公开（公告）日：2011-09-29

  The present invention relates to the identification of compounds and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided compounds.

  本发明涉及识别用于治疗肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的化合物和药物组合物，还提供了制备所述化合物的方法。
• Treatment of Amyotrophic Lateral Sclerosis
  申请人：Northwestern University

  公开号：US20150018388A1

  公开（公告）日：2015-01-15

  The present invention relates to the identification of compounds and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided compounds.

  本发明涉及识别化合物和制药组合物，用于治疗患有肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的患者。本发明还提供了制备所提供化合物的方法。
• Treatment of amyotrophic lateral sclerosis
  申请人：Northwestern University

  公开号：US09145424B2

  公开（公告）日：2015-09-29

  The present invention relates to the identification of compounds and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided compounds.

  本发明涉及识别化合物和制备药物组合物，用于治疗患有肌萎缩侧索硬化（ALS）和其他神经退行性疾病的患者。本发明还提供了制备所提供的化合物的方法。
• [EN] TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS<br/>[FR] TRAITEMENT DE LA SCLÉROSE LATÉRALE AMYOTROPHIQUE
  申请人：CAMBRIA PHARMACEUTICALS INC

  公开号：WO2010059241A3

  公开（公告）日：2010-09-16
• PYRAZOLONE DERIVATIVES USEFUL IN THE TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS
  申请人：Northwestern University

  公开号：EP2367798B1

  公开（公告）日：2018-02-28