2,3-dibromo-4-(4-fluorophenyl)-1-methyl-5-<4-(methylsulfonyl)phenyl>-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,3-dibromo-4-(4-fluorophenyl)-1-methyl-5-<4-(methylsulfonyl)phenyl>-1H-pyrrole
• 英文别名: 2,3-Dibromo-4-(4-fluoro-phenyl)-5-(4-methanesulfonyl-phenyl)-1-methyl-1H-pyrrole；2,3-dibromo-4-(4-fluorophenyl)-1-methyl-5-(4-methylsulfonylphenyl)pyrrole
• 化学式: C₁₈H₁₄Br₂FNO₂S
• 分子量: 487.187
• InChiKey: QFDFHJQXZHCYDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-<4-(methylsulfonyl)phenyl>-3-(4-fluorophenyl)-1H-pyrrole 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2,3-dibromo-4-(4-fluorophenyl)-1-methyl-5-<4-(methylsulfonyl)phenyl>-1H-pyrrole
  参考文献：
  名称：

  Antiinflammatory 4,5-Diarylpyrroles: Synthesis and QSAR

  摘要：

  A series of 2-substituted- and 2,3-disubstituted-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrroles was synthesized and found to be active in the rat adjuvant arthritis model of inflammation. The most active compounds were the 2-halo derivatives in the order of chloro > bromo > iodo. The same pattern of activity was observed for the 2,3-dihalopyrroles. Quantitative structure-activity relationship studies suggested that the activity could be correlated with the molar refractivity and the inductive field effect of the 2-substituent and the lipophilicity of the 3-substituent.

  DOI：

  10.1021/jm00033a017

文献信息

• Wilkerson Wendell W., Galbraith William, Gans-Brangs Kathleen, Grubb Mary+, J. Med. Chem., 37 (1994) N 7, S 988-998
  作者：Wilkerson Wendell W., Galbraith William, Gans-Brangs Kathleen, Grubb Mary+

  DOI：——

  日期：——
• Antiinflammatory 4,5-Diarylpyrroles: Synthesis and QSAR
  作者：Wendell W. Wilkerson、William Galbraith、Kathleen Gans-Brangs、Mary Grubb、Walter E. Hewes、Bruce Jaffee、J. P. Kenney、Janet Kerr、Nancy Wong

  DOI：10.1021/jm00033a017

  日期：1994.4

  A series of 2-substituted- and 2,3-disubstituted-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrroles was synthesized and found to be active in the rat adjuvant arthritis model of inflammation. The most active compounds were the 2-halo derivatives in the order of chloro > bromo > iodo. The same pattern of activity was observed for the 2,3-dihalopyrroles. Quantitative structure-activity relationship studies suggested that the activity could be correlated with the molar refractivity and the inductive field effect of the 2-substituent and the lipophilicity of the 3-substituent.