2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile | 954112-86-8

• 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-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
• CAS: 954112-86-8
• 化学式: C₁₄H₉N₃
• 分子量: 219.246
• InChiKey: AASUBSIWRTWXTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile 、 乙二胺 在 diphosphorus pentasulfide 作用下， 反应 5.0h， 以66%的产率得到3-(4,5-dihydro-1H-imidazol-2-yl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines

  摘要：

  In the present investigation, two series of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines (2a-1) and thieno[2,3-b]pyridines (3a-1) were designed as analogs of BL 11282 (1). The in vitro glucose dependent insulinotropic activity of all the test compounds was evaluated using RIN5F cell based assay and all the test compounds showed glucose and concentration dependent insulin secretion. The in vivo antidiabetic activities of most potent compounds from each series (2c and 3c) were assessed in C57BL/6J mice. Compounds 2c and 3c showed dose dependent insulin secretion and significant glucose reduction in vivo. In general, compounds 2c and 3c were found to be equipotent at all the three different doses selected and with respect to BL 11282, both the test compounds were found to be more potent, at all the time points. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.005
• 作为产物：
  描述：

  2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime 在 乙酸酐 、 水 作用下， 反应 7.0h， 以68%的产率得到2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines

  摘要：

  In the present investigation, two series of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines (2a-1) and thieno[2,3-b]pyridines (3a-1) were designed as analogs of BL 11282 (1). The in vitro glucose dependent insulinotropic activity of all the test compounds was evaluated using RIN5F cell based assay and all the test compounds showed glucose and concentration dependent insulin secretion. The in vivo antidiabetic activities of most potent compounds from each series (2c and 3c) were assessed in C57BL/6J mice. Compounds 2c and 3c showed dose dependent insulin secretion and significant glucose reduction in vivo. In general, compounds 2c and 3c were found to be equipotent at all the three different doses selected and with respect to BL 11282, both the test compounds were found to be more potent, at all the time points. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.005