3,3'-bipyridine bisbenzonitrile | 916653-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,3'-bipyridine bisbenzonitrile
• 英文别名: 4-[5-[6-(4-Cyanophenyl)pyridin-3-yl]pyridin-2-yl]benzonitrile
• CAS: 916653-47-9
• 化学式: C₂₄H₁₄N₄
• 分子量: 358.402
• InChiKey: DDVPVISGVLSTFS-UHFFFAOYSA-N

物化性质

• 沸点：
  644.1±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-bipyridine bisbenzonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到4,4'-[(3,3'-bipyridine)-6,6'-diyl]dibenzamidine tetrahydrochloride
  参考文献：
  名称：

  Pentamidine analogs as inhibitors of [3H]MK-801 and [3H]ifenprodil binding to rat brain NMDA receptors

  摘要：

  The anti-protozoal drug pentamidine is active against opportunistic Pneumocystis pneumonia, but in addition has several other biological targets, including the NMDA receptor (NR). Here we describe the inhibitory potencies of 76 pentamidine analogs at 2 binding sites of the NR, the channel binding site labeled with [H-3]MK-801 and the [H-3]ifenprodil binding site. Most analogs acted weaker at the ifenprodil than at the channel site. The spermine-sensitivity of NR inhibition by the majority of the compounds was reminiscent of other long-chain dicationic NR blockers. The potency of the parent compound as NR blocker was increased by modifying the heteroatoms in the bridge connecting the 2 benzamidine moieties and also by integrating the bridge into a seven-membered ring. Docking of the 45 most spermine-sensitive bisbenzamidines to a recently described acidic interface between the N-terminal domains of GluN1 and GluN2B mediating polyamine stimulation of the NR revealed the domain contributed by GluN1 as the most relevant target. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.012
• 作为产物：
  描述：

  4-(5-bromopyridin-2-yl)benzonitrile 在 四(三苯基膦)钯 、 六正丁基二锡 作用下， 以77%的产率得到3,3'-bipyridine bisbenzonitrile
  参考文献：
  名称：

  Pentamidine analogs as inhibitors of [3H]MK-801 and [3H]ifenprodil binding to rat brain NMDA receptors

  摘要：

  The anti-protozoal drug pentamidine is active against opportunistic Pneumocystis pneumonia, but in addition has several other biological targets, including the NMDA receptor (NR). Here we describe the inhibitory potencies of 76 pentamidine analogs at 2 binding sites of the NR, the channel binding site labeled with [H-3]MK-801 and the [H-3]ifenprodil binding site. Most analogs acted weaker at the ifenprodil than at the channel site. The spermine-sensitivity of NR inhibition by the majority of the compounds was reminiscent of other long-chain dicationic NR blockers. The potency of the parent compound as NR blocker was increased by modifying the heteroatoms in the bridge connecting the 2 benzamidine moieties and also by integrating the bridge into a seven-membered ring. Docking of the 45 most spermine-sensitive bisbenzamidines to a recently described acidic interface between the N-terminal domains of GluN1 and GluN2B mediating polyamine stimulation of the NR revealed the domain contributed by GluN1 as the most relevant target. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.012

文献信息

• Linear dicationic terphenyls and their aza analogues as antiparasitic agents
  申请人：Tidwell R. Richard

  公开号：US20070232621A1

  公开（公告）日：2007-10-04

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二价离子三苯基化合物及其氮杂环类似物。使用小说二价离子三苯基化合物及其氮杂环类似物对微生物感染进行作战的方法。合成小说二价离子三苯基化合物及其氮杂环类似物的过程。
• NOVEL TERARYL COMPOUNDS AS ANTIPARASITIC AGENTS
  申请人：Tidwell Richard R.

  公开号：US20110257199A1

  公开（公告）日：2011-10-20

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二元离子三苯基化合物及其氮杂环类似物。使用小说二元离子三苯基化合物及其氮杂环类似物对抗微生物感染的方法。合成小说二元离子三苯基化合物及其氮杂环类似物的过程。
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  公开号：US7964619B2

  公开（公告）日：2011-06-21
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