5-(4-chlorophenyl)-N-(1-adamantyl)-1-(2,4-dichlorophenyl)-1H-1,2,4-triazole-3-carboxamide

• 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-(4-chlorophenyl)-N-(1-adamantyl)-1-(2,4-dichlorophenyl)-1H-1,2,4-triazole-3-carboxamide
• 英文别名: N-(1-adamantyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1,2,4-triazole-3-carboxamide
• 化学式: C₂₅H₂₃Cl₃N₄O
• 分子量: 501.843
• InChiKey: QUTCNGZZFVRBKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二氯苯胺 在 吡啶 、 tetrafluoroboric acid 、 溴 、 三甲基铝 、 sodium acetate 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 正庚烷 、 二氯甲烷 、 水 为溶剂， 反应 336032.5h， 生成 5-(4-chlorophenyl)-N-(1-adamantyl)-1-(2,4-dichlorophenyl)-1H-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Structural–activity relationship study on C-4 carbon atom of the CB1 antagonist SR141716: synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides

  摘要：

  A series of 1,2,4-triazole-3-carboxamides has been prepared from alkyl-1,2,4-triazole-3-carboxylates under mild conditions. The ability of these triazoles to displace [H-3]-CP55940 from CB1 cannabinoid receptor was measured. However, they showed only poor to moderate binding affinities, indicating that substitution of the C-4 pyrazole atom of the CB1 reference compound SR141716 by a nitrogen atom results in loss of affinity. Further investigations for functionality indicated that the compound 6a exhibited significant cannabinoid antagonistic properties in the mouse vas deferens functional assay. This leads us to the conclusion that 6a binds at a different CB, binding site or at a new cannabinoid receptor subtype. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.06.012

文献信息

• [EN] NEW 1,2,4-TRIAZOLE-3-CARBOXAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES 1,2,4-TRIAZOLE-3-CARBOXAMIDE
  申请人：ESTEVE LABOR DR

  公开号：WO2006030285A1

  公开（公告）日：2006-03-23

  The invention relates to new 1,2,4-triazole-3-carboxamide derivatives, as well as to their use for the treatment of diseases in which cannabinoid receptors are involved.

  这项发明涉及新的1,2,4-三唑-3-羧酰胺衍生物，以及它们用于治疗涉及大麻素受体的疾病。