2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyrimidine | 909104-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyrimidine
• 英文别名: 2-(4-Chlorophenyl)-3-phenylimidazo[1,2-a]pyrimidine
• CAS: 909104-27-4
• 化学式: C₁₈H₁₂ClN₃
• 分子量: 305.766
• InChiKey: JHOOLARAHNNRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyrimidine 在 肼 作用下， 以 乙腈 为溶剂， 反应 0.42h， 生成 5-(4-chlorophenyl)-4-phenyl-1H-imidazol-2-amine
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 在 tetrafluoroboric acid 、 碳酸氢钠 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  使用叶绿素作为生物催化剂和重氮盐对咪唑并[1,2-a]吡啶衍生物进行光化学区域选择性 C-H 芳基化

  摘要：

  该通讯描述了一种温和的方法，用于用重氮盐衍生物芳基化咪唑并[1,2- a ]吡啶，并通过可见光催化使用叶绿素作为生物催化剂。叶绿素等天然色素被用作绿色光敏剂和对环境无害的催化剂。通用且简单的程序为在环境温度下以良好至极好的收率形成 2,3-二芳基咪唑并[1,2- a ] 吡啶衍生物提供了一种不含过渡金属的替代方案。

  DOI：

  10.1039/d1nj06059g