5-hydroxymethyl-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-4-phenylpyrazole | 265643-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-hydroxymethyl-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-4-phenylpyrazole
• 英文别名: [3-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-4-phenyl-1H-pyrazol-5-yl]methanol
• CAS: 265643-68-3
• 化学式: C₁₄H₁₅N₅O₂
• 分子量: 285.305
• InChiKey: JLHKCPHLGGXAQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-4-phenylpyrazole 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以90%的产率得到3-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-4-phenyl-1H-pyrazole-5-carbaldehyde
  参考文献：
  名称：

  2,3,7-Trisubstituted pyrazolo[1,5-d][1,2,4]triazines: Functionally selective GABAA α3-subtype agonists

  摘要：

  Novel synthetic routes have been devised for the preparation of previously inaccessible 2,3,7-trisubstituted pyrazolo[1,5-d][1,2,4]triazines 2. These compounds are high affinity ligands for the GABA(A) benzodiazepine binding site and some analogues show functional selectivity for agonism at alpha 3-containing receptors over alpha 1-containing receptors with the lead compound being 32. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.081
• 作为产物：
  描述：

  5-Hydroxymethyl-4-phenyl-1H-pyrazol-3-ol 、 5-氯甲基-1-甲基-1H-[1,2,4]噻唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以38%的产率得到5-hydroxymethyl-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-4-phenylpyrazole
  参考文献：
  名称：

  2,3,7-Trisubstituted pyrazolo[1,5-d][1,2,4]triazines: Functionally selective GABAA α3-subtype agonists

  摘要：

  Novel synthetic routes have been devised for the preparation of previously inaccessible 2,3,7-trisubstituted pyrazolo[1,5-d][1,2,4]triazines 2. These compounds are high affinity ligands for the GABA(A) benzodiazepine binding site and some analogues show functional selectivity for agonism at alpha 3-containing receptors over alpha 1-containing receptors with the lead compound being 32. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.081

文献信息

• Pyrazolo-triazine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06476030B1

  公开（公告）日：2002-11-05

  Compounds according to Formula (I): or a salt or prodrug thereof, have good affinity as ligands for the alpha2 and/or alpha3 subunit of the human GABAA receptor and are useful for treatment of disorders of the central nervous system, including anxiety and convulsions.

  根据公式（I）合成的化合物或其盐或前药，具有良好的亲和力作为人类GABAA受体的α2和/或α3亚基的配体，并且对于治疗中枢神经系统疾病，包括焦虑和抽搐，是有用的。
• PYRAZOLO-TRIAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS
  申请人：Merck Sharp & Dohme Limited

  公开号：EP1121361A1

  公开（公告）日：2001-08-08
• US6476030B1
  申请人：——

  公开号：US6476030B1

  公开（公告）日：2002-11-05
• [EN] PYRAZOLO-TRIAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES PYRAZOLO-TRIAZINE UTILISES EN TANT QUE LIGANDS DES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2000023449A1

  公开（公告）日：2000-04-27

  A class of substituted pyrazolo[1,5-d][1,2,4]triazine derivatives, possessing an optionally substituted cycloalkyl, phenyl or heteroaryl substituent at the 7-position and a substituted alkoxy moiety at the 2-position, are selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.