5-methyl-1-[3-(methyloxy)phenyl]-1H-1,2,3-triazole-4-carboxylic acid | 386264-51-3

• 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-methyl-1-[3-(methyloxy)phenyl]-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 1-(3-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid；1-(3-methoxyphenyl)-5-methyltriazole-4-carboxylic acid
• CAS: 386264-51-3
• 化学式: C₁₁H₁₁N₃O₃
• mdl: MFCD07397772
• 分子量: 233.227
• InChiKey: GMCAEMVOKZCERW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-1-[3-(methyloxy)phenyl]-1H-1,2,3-triazole-4-carboxylic acid 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 以88%的产率得到1-(3-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl chloride
  参考文献：
  名称：

  Synthesis of 1,2,4- and 1,3,4-oxadiazoles from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides

  摘要：

  5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N'-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N'-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles.

  DOI：

  10.1134/s1070428008100217
• 作为产物：
  描述：

  1-叠氮基-3-甲氧基苯 在 sodium hydroxide 作用下， 生成 5-methyl-1-[3-(methyloxy)phenyl]-1H-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents

  摘要：

  DOI：

  10.1016/j.molstruc.2021.131146

文献信息

• [EN] TRIAZOLE AMIDE DERIVATIVES FOR USE IN THERAPY<br/>[FR] DÉRIVÉS AMIDES DE TRIAZOLE DESTINÉS À ÊTRE UTILISÉS EN THÉRAPIE
  申请人：GLAXO GROUP LTD

  公开号：WO2009115486A1

  公开（公告）日：2009-09-24

  The invention relates to triazole amide derivatives of formula (I) for use in therapy, in particular for treating diseases and conditions mediated by antagonism of the mGluR5 receptor, in particular substance related disorders. The invention also relates to certain novel derivatives. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

  该发明涉及公式（I）的三唑酰胺衍生物，用于治疗特定由mGluR5受体拮抗介导的疾病和症状，特别是物质相关障碍。该发明还涉及某些新颖的衍生物。此外，该发明涉及含有这些衍生物的组合物以及它们的制备方法。
• TRIAZOLE AMIDE DERIVATIVES FOR USE IN THERAPY
  申请人：Garzya Vincenzo

  公开号：US20110065725A1

  公开（公告）日：2011-03-17

  The invention relates to triazole amide derivatives of formula (I) for use in therapy, in particular for treating diseases and conditions mediated by antagonism of the mGluR 5 receptor, in particular substance related disorders. The invention also relates to certain novel derivatives. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

  本发明涉及式（I）的三唑酰胺衍生物，用于治疗疾病和条件，特别是通过拮抗mGluR5受体介导的物质相关障碍。本发明还涉及某些新颖的衍生物。此外，本发明涉及含有这些衍生物的组合物和它们的制备方法。
• Design and Optimization of 1<i>H</i>-1,2,3-Triazole-4-carboxamides as Novel, Potent, and Selective Inverse Agonists and Antagonists of PXR
  作者：Yongtao Li、Wenwei Lin、Sergio C. Chai、Jing Wu、Kavya Annu、Taosheng Chen

  DOI：10.1021/acs.jmedchem.2c01640

  日期：2022.12.22

  selective and the most potent inverse agonist and antagonist of PXR, with low nanomolar IC50 values for binding and cellular activity. Importantly, compound 89, a close analog of 85, is a selective and pure antagonist with low nanomolar IC50 values for binding and cellular activity. This study has provided novel, selective, and most potent PXR inhibitors (a dual inverse agonist/antagonist and a pure antagonist)

  孕烷 X 受体 (PXR) 是药物代谢的关键调节因子。许多药物结合并激活 PXR，导致药物不良反应。这表明PXR抑制剂具有治疗价值，但迄今为止缺乏有效的PXR抑制剂。在此，我们报告了一系列 1 H -1,2,3-三唑-4-甲酰胺化合物的结构优化，从而发现化合物85作为 PXR 的选择性且最有效的反向激动剂和拮抗剂，具有低结合和细胞活性的纳摩尔 IC 50值。重要的是，化合物89是85的密切类似物，是一种选择性纯拮抗剂，其结合和细胞活性具有低纳摩尔 IC 50值。这项研究为基础研究和未来的临床研究提供了新型、选择性和最有效的 PXR 抑制剂（双重反向激动剂/拮抗剂和纯拮抗剂），并揭示了如何降低化合物与 PXR 的结合亲和力。
• Synthesis of 1,2,4- and 1,3,4-oxadiazoles from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides
  作者：N. D. Obushak、N. T. Pokhodylo、N. I. Pidlypnyi、V. S. Matiichuk

  DOI：10.1134/s1070428008100217

  日期：2008.10

  5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N'-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N'-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles.
• Chu; Sun; Zhang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 9, p. 854 - 856
  作者：Chu、Sun、Zhang、Li、Liao

  DOI：——

  日期：——