3-(4-bromophenyl)-4-(2-fluorophenyl)-5-methyl-4H-1,2,4-triazole | 374889-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-bromophenyl)-4-(2-fluorophenyl)-5-methyl-4H-1,2,4-triazole
• 英文别名: 3-(4-Bromophenyl)-4-(2-fluorophenyl)-5-methyl-1,2,4-triazole
• CAS: 374889-98-2
• 化学式: C₁₅H₁₁BrFN₃
• 分子量: 332.175
• InChiKey: IPMYISOUMXBKHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-4-(2-fluorophenyl)-5-methyl-4H-1,2,4-triazole 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 5.83h， 生成 3-{4-[4-(2-fluorophenyl)-5-methyl-4H-1,2,4-triazol-3-yl]-phenyl}pyridine
  参考文献：
  名称：

  Atropisomeric 4-Phenyl-4H-1,2,4-triazoles as Selective Glycine Transporter 1 Inhibitors

  摘要：

  We report on the optimization of 4H-1,2,4-triazole derivatives to increase their activity and selectivity as glycine transporter 1 (GlyT1) inhibitors. Structure-activity relationship exploration resulted in the identification of a 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methyl-benzonitrile (14u) compound with markedly higher selectivity for GlyT1. Physiochemical studies revealed that 14u exists as a stable pair of atropisomers under physiological conditions. We successfully separated the atropisomers to obtain active enantiomer (R)-14u, which displayed favorable pharmacokinetic properties, as well as positive results in the mice Y-maze test.

  DOI：

  10.1021/jm400383w
• 作为产物：
  描述：

  N-(2-fluorophenyl)ethanethioamide 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 3-(4-bromophenyl)-4-(2-fluorophenyl)-5-methyl-4H-1,2,4-triazole
  参考文献：
  名称：

  Atropisomeric 4-Phenyl-4H-1,2,4-triazoles as Selective Glycine Transporter 1 Inhibitors

  摘要：

  We report on the optimization of 4H-1,2,4-triazole derivatives to increase their activity and selectivity as glycine transporter 1 (GlyT1) inhibitors. Structure-activity relationship exploration resulted in the identification of a 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methyl-benzonitrile (14u) compound with markedly higher selectivity for GlyT1. Physiochemical studies revealed that 14u exists as a stable pair of atropisomers under physiological conditions. We successfully separated the atropisomers to obtain active enantiomer (R)-14u, which displayed favorable pharmacokinetic properties, as well as positive results in the mice Y-maze test.

  DOI：

  10.1021/jm400383w

文献信息

• Triazole derivatives
  申请人：——

  公开号：US20030216385A1

  公开（公告）日：2003-11-20

  The invention relates to a triazole derivative with an activity inhibiting glycine transporter and for use as a pharmaceutical drug, and a novel triazole derivative. The inventive triazole derivative has an excellent activity inhibiting glycine transporter and is useful as a therapeutic agent of dementia, schizophrenia, cognitive disorders, or cognitive disorders involved in various diseases such as Alzheimer disease, Parkinson's disease, or Huntington disease or the like, or spasm involved in diseases such as nerve degenerative diseases and cerebrovascular disorders, or the like. Particularly, the pharmaceutical drug is useful for the amelioration of learning disability of dementia and the like.

  该发明涉及一种三唑衍生物，具有抑制甘氨酸转运体活性，并用作药物，以及一种新颖的三唑衍生物。这种创新的三唑衍生物具有出色的抑制甘氨酸转运体活性，并可用作治疗痴呆症、精神分裂症、认知障碍或涉及各种疾病如阿尔茨海默病、帕金森病、亨廷顿病等的认知障碍，或涉及神经退行性疾病和脑血管疾病等疾病的痉挛。特别是，这种药物对改善痴呆症等学习障碍非常有用。
• Triazole derivative
  申请人：YAMANOUCHI PHARMACEUTICAL CO., LTD., MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG

  公开号：US20040214818A1

  公开（公告）日：2004-10-28

  The invention relates to a triazole derivative with an activity inhibiting glycine transporter and for use as a pharmaceutical drug, and a novel triazole derivative. The inventive triazole derivative has an excellent activity inhibiting glycine transporter and is useful as a therapeutic agent of dementia, schizophrenia, cognitive disorders, or cognitive disorders involved in various diseases such as Alzheimer disease, Parkinson's disease, or Huntington disease or the like, or spasm involved in diseases such as nerve degenerative diseases and cerebrovascular disorders, or the like. Particularly, the pharmaceutical drug is useful for the amelioration of learning disability of dementia and the like.

  该发明涉及一种三唑衍生物，具有抑制甘氨酸转运体的活性，用作药物，并且是一种新型的三唑衍生物。该三唑衍生物具有优异的抑制甘氨酸转运体的活性，可用作治疗痴呆症、精神分裂症、认知障碍或涉及各种疾病的认知障碍，如阿尔茨海默病、帕金森病或亨廷顿病等，或涉及神经退行性疾病和脑血管疾病等痉挛。特别地，该药物对改善痴呆症等学习障碍非常有用。
• TRIAZOLE DERIVATIVES
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1293503A1

  公开（公告）日：2003-03-19

  The invention relates to a triazole derivative with an activity inhibiting glycine transporter and for use as a pharmaceutical drug, and a novel triazole derivative. The inventive triazole derivative has an excellent activity inhibiting glycine transporter and is useful as a therapeutic agent of dementia, schizophrenia, cognitive disorders, or cognitive disorders involved in various diseases such as Alzheimer disease, Parkinson's disease, or Huntington disease or the like, or spasm involved in diseases such as nerve degenerative diseases and cerebrovascular disorders, or the like. Particularly, the pharmaceutical drug is useful for the amelioration of learning disability of dementia and the like.

  本发明涉及一种具有抑制甘氨酸转运体活性并可用作药物的三唑衍生物，以及一种新型三唑衍生物。本发明的三唑衍生物具有良好的抑制甘氨酸转运体的活性，可作为痴呆症、精神分裂症、认知障碍或阿尔茨海默病、帕金森病或亨廷顿病等各种疾病所涉及的认知障碍，或神经变性疾病和脑血管疾病等疾病所涉及的痉挛等的治疗药物。特别是，该药物可用于改善痴呆症等的学习障碍。
• US7034047B2
  申请人：——

  公开号：US7034047B2

  公开（公告）日：2006-04-25
• US7084164B2
  申请人：——

  公开号：US7084164B2

  公开（公告）日：2006-08-01