N-(4-cyanophenyl)-4-(4-cyanobenzylidinyl)piperidine | 182201-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(4-cyanophenyl)-4-(4-cyanobenzylidinyl)piperidine
• 英文别名: 4-[[1-(4-Cyanophenyl)piperidin-4-ylidene]methyl]benzonitrile
• CAS: 182201-44-1
• 化学式: C₂₀H₁₇N₃
• 分子量: 299.375
• InChiKey: SOKMJLDGIONMGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-cyanophenyl)-4-(4-cyanobenzylidinyl)piperidine 在 5percent Pd/C 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q
• 作为产物：
  描述：

  对氟苯腈 在 吡啶 、 sodium hydride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 N-(4-cyanophenyl)-4-(4-cyanobenzylidinyl)piperidine
  参考文献：
  名称：

  Synthesis and anti-pneumocystis carinii activity of piperidine-linked aromatic diimidazolines

  摘要：

  A series of novel piperidine-linked aromatic diimidazolines (3-7) have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii drug, Pentamidine. These compounds significantly inhibited the growth of Pneumocystis carinii in culture at 1 mu g/mL. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00373-3

文献信息

• Synthesis and anti-pneumocystis carinii activity of piperidine-linked aromatic diimidazolines
  作者：Tien L. Huang、Qian Zhang、Angele T. White、Sherry F. Queener、Marilyn S. Bartlett、James W. Smith、Isaac O. Donkor

  DOI：10.1016/0960-894x(96)00373-3

  日期：1996.9

  A series of novel piperidine-linked aromatic diimidazolines (3-7) have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii drug, Pentamidine. These compounds significantly inhibited the growth of Pneumocystis carinii in culture at 1 mu g/mL. Copyright (C) 1996 Elsevier Science Ltd
• Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners
  作者：Isaac O. Donkor、Tien L. Huang、Bin Tao、Donna Rattendi、Schennella Lane、Marc Vargas、Burt Goldberg、Cyrus Bacchi

  DOI：10.1021/jm020375q

  日期：2003.3.1

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.