5-bromo-3-(4-fluorophenyl)-1-methyl-4-pyridin-4-yl-1H-pyrrole-2-carbonitrile | 678163-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-bromo-3-(4-fluorophenyl)-1-methyl-4-pyridin-4-yl-1H-pyrrole-2-carbonitrile
• 英文别名: 5-Bromo-3-(4-fluorophenyl)-1-methyl-4-pyridin-4-ylpyrrole-2-carbonitrile
• CAS: 678163-17-2
• 化学式: C₁₇H₁₁BrFN₃
• 分子量: 356.197
• InChiKey: PEJWMTQPUXRCJT-UHFFFAOYSA-N

物化性质

• 沸点：
  429.3±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-3-(4-fluorophenyl)-1-methyl-4-pyridin-4-yl-1H-pyrrole-2-carbonitrile 、 1-乙酰哌嗪 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 以93%的产率得到JNJ-17089540
  参考文献：
  名称：

  Inhibitors of unactivated p38 MAP kinase

  摘要：

  Inhibition of the p38 map kinase pathway has been shown to be beneficial in the treatment of inflammatory diseases. The first class of potent p38 kinase inhibitors was the pyridinylimidazole compounds from SKB. Since then several pyridinylimidazole-based compounds have been shown to inhibit activated p38 kinase in vitro and in vivo. We have developed a novel series of pyridinylimidazole-based compounds, which potently inhibit the p38 pathway by binding to unactivated p38 kinase and only weakly inhibiting activated p38 kinase activity in vitro.

  DOI：

  10.1016/j.bmcl.2006.08.101
• 作为产物：
  描述：

  3-(4-氟苯基)-4-(4-吡啶基)-1H-吡咯-2-甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 氨 、 三甲基铝 、 sodium hydride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 5-bromo-3-(4-fluorophenyl)-1-methyl-4-pyridin-4-yl-1H-pyrrole-2-carbonitrile
  参考文献：
  名称：

  Inhibitors of unactivated p38 MAP kinase

  摘要：

  Inhibition of the p38 map kinase pathway has been shown to be beneficial in the treatment of inflammatory diseases. The first class of potent p38 kinase inhibitors was the pyridinylimidazole compounds from SKB. Since then several pyridinylimidazole-based compounds have been shown to inhibit activated p38 kinase in vitro and in vivo. We have developed a novel series of pyridinylimidazole-based compounds, which potently inhibit the p38 pathway by binding to unactivated p38 kinase and only weakly inhibiting activated p38 kinase activity in vitro.

  DOI：

  10.1016/j.bmcl.2006.08.101

文献信息

• Direct Conversion of Substituted Pyrrole-2-carboxylic Acid Methyl Esters to Their 2-Carbonitrile Analogues
  作者：Xun Li、Michael Reuman、Ronald K. Russell

  DOI：10.3987/com-06-s(w)4

  日期：——

  Small to large quantity (1-136 g) of substituted pyrrole-2-carbonitrles were reproducibly prepared from their corresponding 2-carboxylic acid methyl esters in one step with 53-61% yield and high chemical purity (> 97%), with using dimethylaluminum amide [(CH3)(2)AlNH2] that was freshly generated by treating anhydrous ammonia (NH3) and trimethylaluminum [(CH3)(3)Al] at -40 degrees C in chlorobenzene, a modified Weinreb's method.
• Inhibitors of unactivated p38 MAP kinase
  作者：James Bullington、Dennis Argentieri、Kristin Averill、Demetrius Carter、Druie Cavender、Bohumila Fahmy、Xiaodong Fan、Daniel Hall、Geoffrey Heintzelman、Paul Jackson、Wai-Ping Leung、Xun Li、Ping Ling、Gilbert Olini、Thomas Razler、Michael Reuman、Kenneth Rupert、Ronald Russell、John Siekierka、Scott Wadsworth、Russell Wolff、Bangping Xiang、Yue-Mei Zhang

  DOI：10.1016/j.bmcl.2006.08.101

  日期：2006.12

  Inhibition of the p38 map kinase pathway has been shown to be beneficial in the treatment of inflammatory diseases. The first class of potent p38 kinase inhibitors was the pyridinylimidazole compounds from SKB. Since then several pyridinylimidazole-based compounds have been shown to inhibit activated p38 kinase in vitro and in vivo. We have developed a novel series of pyridinylimidazole-based compounds, which potently inhibit the p38 pathway by binding to unactivated p38 kinase and only weakly inhibiting activated p38 kinase activity in vitro.