1-(4-Bromo-2,6-dichloro-phenyl)-4-butyl-1H-[1,2,3]triazole | 879012-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Bromo-2,6-dichloro-phenyl)-4-butyl-1H-[1,2,3]triazole
• 英文别名: 1-(4-bromo-2,6-dichlorophenyl)-4-butyl-1H-1,2,3-triazole；1-(4-bromo-2,6-dichlorophenyl)-4-butyltriazole
• CAS: 879012-77-8
• 化学式: C₁₂H₁₂BrCl₂N₃
• 分子量: 349.057
• InChiKey: XJWOWBGWORGKJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Bromo-2,6-dichloro-phenyl)-4-butyl-1H-[1,2,3]triazole 在 四丁基氟化铵 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-Butyl-1-(2,6-dichloro-4-ethynyl-phenyl)-1H-[1,2,3]triazole
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Phenyl-1H-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists

  摘要：

  To study the interaction of phenylheterocycles with gamma-aminobutyric acid (GABA) receptors, 4- or 5-alkyl(or phenyl)-1-phenyl-1 H-1,2,3-triazoles were synthesized and examined for their ability to inhibit the specific binding of [H-3]-4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a noncompetitive antagonist, to the housefly and rat GABA receptors, as well as to the beta 3 subunit homo-oligomer of the human GABA receptor investigated as a model receptor. 4-Substituted 1-phenyl-1 H-1,2,3-triazoles were found to be more potent competitive inhibitors than the 5-substituted regioisomers in the case of all receptors. The 4-tert-butyl or 4-n-propyl analogue of 1-(2,6-dichloro-4-trifluoromethylphenyl)1 H-1,2,3-triazole exhibited the highest level of inhibition of [H-3]EBOB binding to all receptors. Most of the synthesized analogues were more active in terms of the inhibition of EBOB binding to the housefly and human beta 3 GABA receptors than to the rat receptor. The 4-cyclohexyl analogue showed the highest (185-fold) housefly versus rat receptor selectivity. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis demonstrated that both the 4-trifluoromethyl-2,6dichloro substitution on the phenyl ring and a small, bulky, hydrophobic substituent at the 4-position of the triazole ring played significant roles in conferring high potency in cases involving the housefly and human beta 3 receptors. The human beta 3 receptor resembled the housefly receptor in terms of their recognition of phenyltriazoles, whereas 3D-QSAR analysis revealed a slight difference between the two receptors in terms of their mechanisms of recognition of the para-substituent on the phenyl moiety. Some of the triazoles synthesized here exhibited insecticidal activity, which was correlated with their ability to inhibit [H-3]EBOB binding to the housefly receptor. Thus, 1-phenyl-1 H-1,2,3-triazoles with the appropriate substituents exert insecticidal activity by selectively acting at the site for noncompetitive antagonism of insect GABA receptors.

  DOI：

  10.1021/jf052773i
• 作为产物：
  描述：

  4-溴-2,6-二氯苯胺 在 盐酸 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 16.5h， 生成 1-(4-Bromo-2,6-dichloro-phenyl)-4-butyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Phenyl-1H-1,2,3-triazoles as Selective Insect GABA Receptor Antagonists

  摘要：

  To study the interaction of phenylheterocycles with gamma-aminobutyric acid (GABA) receptors, 4- or 5-alkyl(or phenyl)-1-phenyl-1 H-1,2,3-triazoles were synthesized and examined for their ability to inhibit the specific binding of [H-3]-4'-ethynyl-4-n-propylbicycloorthobenzoate (EBOB), a noncompetitive antagonist, to the housefly and rat GABA receptors, as well as to the beta 3 subunit homo-oligomer of the human GABA receptor investigated as a model receptor. 4-Substituted 1-phenyl-1 H-1,2,3-triazoles were found to be more potent competitive inhibitors than the 5-substituted regioisomers in the case of all receptors. The 4-tert-butyl or 4-n-propyl analogue of 1-(2,6-dichloro-4-trifluoromethylphenyl)1 H-1,2,3-triazole exhibited the highest level of inhibition of [H-3]EBOB binding to all receptors. Most of the synthesized analogues were more active in terms of the inhibition of EBOB binding to the housefly and human beta 3 GABA receptors than to the rat receptor. The 4-cyclohexyl analogue showed the highest (185-fold) housefly versus rat receptor selectivity. A three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis demonstrated that both the 4-trifluoromethyl-2,6dichloro substitution on the phenyl ring and a small, bulky, hydrophobic substituent at the 4-position of the triazole ring played significant roles in conferring high potency in cases involving the housefly and human beta 3 receptors. The human beta 3 receptor resembled the housefly receptor in terms of their recognition of phenyltriazoles, whereas 3D-QSAR analysis revealed a slight difference between the two receptors in terms of their mechanisms of recognition of the para-substituent on the phenyl moiety. Some of the triazoles synthesized here exhibited insecticidal activity, which was correlated with their ability to inhibit [H-3]EBOB binding to the housefly receptor. Thus, 1-phenyl-1 H-1,2,3-triazoles with the appropriate substituents exert insecticidal activity by selectively acting at the site for noncompetitive antagonism of insect GABA receptors.

  DOI：

  10.1021/jf052773i