3-dimethylamino-1-[4-(4-fluorophenoxy)phenyl]-propenone

• 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-dimethylamino-1-[4-(4-fluorophenoxy)phenyl]-propenone
• 英文别名: (E)-1-(4-(4-Fluorophenoxy)phenyl)-3-(dimethylamino)prop-2-en-1-one；(E)-3-(dimethylamino)-1-[4-(4-fluorophenoxy)phenyl]prop-2-en-1-one
• 化学式: C₁₇H₁₆FNO₂
• 分子量: 285.318
• InChiKey: AENNHUHISIWUAQ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-1-[4-(4-fluorophenoxy)phenyl]-propenone 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以5.3 g的产率得到3-[4-(4-fluorophenoxy)phenyl]-1H-pyrazole
  参考文献：
  名称：

  3-(4-Phenoxyphenyl)pyrazoles:  A Novel Class of Sodium Channel Blockers

  摘要：

  A series of 3-(4-phenoxyphenyl)-1H-pyrazoles were synthesized and characterized as potent state-dependent sodium channel blockers. A limited SAR study was carried out to delineate the chemical requirements for potency. The results indicate that the distal phenyl group is critical for activity but will tolerate lipophilic (+ pi) electronegative (+ sigma) substituents at the ortho and/or para position. Substitution at the pyrazole nitrogen with a H-bond donor improves potency. Compound 18 showed robust activity in the rat Chung neuropathy paradigm.

  DOI：

  10.1021/jm030498q
• 作为产物：
  描述：

  4-氟苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-dimethylamino-1-[4-(4-fluorophenoxy)phenyl]-propenone
  参考文献：
  名称：

  3-(4-Phenoxyphenyl)pyrazoles:  A Novel Class of Sodium Channel Blockers

  摘要：

  A series of 3-(4-phenoxyphenyl)-1H-pyrazoles were synthesized and characterized as potent state-dependent sodium channel blockers. A limited SAR study was carried out to delineate the chemical requirements for potency. The results indicate that the distal phenyl group is critical for activity but will tolerate lipophilic (+ pi) electronegative (+ sigma) substituents at the ortho and/or para position. Substitution at the pyrazole nitrogen with a H-bond donor improves potency. Compound 18 showed robust activity in the rat Chung neuropathy paradigm.

  DOI：

  10.1021/jm030498q

文献信息

• Aryl substituted pyrazoles, and pyrroles, and the use thereof
  申请人：Euro-Celtique S.A.

  公开号：US06414011B1

  公开（公告）日：2002-07-02

  This invention relates to compounds having the Formula I: or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein Het and R5-R13 are set in the specification. The invention also is directed to the use of compounds of Formula I for the treatment of neuronal damage following global and focal ischemia, for the treatment or prevention of neurodegenerative conditions such as amyotrophic lateral sclerosis (ALS), and for the treatment, prevention or amelioration of both acute or chronic pain, as antitinnitus agents, as anticonvulsants, and as antimanic depressants, as local anesthetics, as antiarrhythmics and for the treatment or prevention of diabetic neuropathy.

  这项发明涉及具有以下化学式I的化合物： 或其药学上可接受的盐、前药或溶剂化合物，其中Het和R5-R13在规范中设置。该发明还涉及化合物I的用途，用于治疗全脑和局部缺血后的神经损伤，用于治疗或预防神经退行性疾病，如肌萎缩侧索硬化症（ALS），以及用于治疗、预防或改善急性或慢性疼痛，作为抗耳鸣剂，作为抗癫痫药，作为抗躁郁药，作为局部麻醉药，作为抗心律失常药，以及用于治疗或预防糖尿病性神经病变。
• Aryl substituted pyridines, pyrimidines, pyrazines and triazines and the use thereof
  申请人：——

  公开号：US20020040025A1

  公开（公告）日：2002-04-04

  This invention relates aryl substituted pyridines, pyrimidines, pyrazines and triazines of Formula I: 1 or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein A 1 , A 2 , A 3 , R 1 -R 4 , X and Y are set in the specification. The invention is also directed to the use of compounds of Formula I for the treatment of neuronal damage following global and focal ischemia, for the treatment or prevention of neurodegenerative conditions such as amyotrophic lateral sclerosis (ALS), and for the treatment, prevention or amelioration of both acute or chronic pain, as antitinnitus agents, as anticonvulsants, and as antimanic depressants, as local anesthetics, as antiarrhythmics and for the treatment or prevention of diabetic neuropathy.

  该发明涉及式I的芳基取代吡啶、嘧啶、吡嗪和三嗪，或其药用可接受的盐、前药或溶剂化合物，其中A1、A2、A3、R1-R4、X和Y在规范中设定。该发明还涉及利用式I的化合物治疗全球性和局部性缺血后的神经损伤，治疗或预防神经退行性疾病，如肌萎缩性侧索硬化（ALS），以及治疗、预防或改善急性或慢性疼痛，作为抗耳鸣剂，抗抽搐剂，抗躁郁症药物，局部麻醉剂，抗心律失常药物，以及治疗或预防糖尿病性神经病变。
• ARYL SUBSTITUTED PYRIDINES, PYRIMIDINES, PYRAZINES AND TRIAZINES AND THE USE THEREOF
  申请人：Euro-Celtique S.A.

  公开号：EP1265866B1

  公开（公告）日：2010-07-21