N,N'-bis-(4-cyanophenyl)homopiperazine | 232923-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis-(4-cyanophenyl)homopiperazine
• 英文别名: N,N'-bis(4-cyanophenyl)homopiperazine；bis(4-cyanophenyl)homopiperazine；4-[4-(4-Cyanophenyl)-1,4-diazepan-1-yl]benzonitrile
• CAS: 232923-90-9
• 化学式: C₁₉H₁₈N₄
• 分子量: 302.379
• InChiKey: BQCZCFULEDZERN-UHFFFAOYSA-N

物化性质

• 沸点：
  548.8±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(4-cyanophenyl)homopiperazine 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 生成 N'-propan-2-yl-4-[4-[4-(N'-propan-2-ylcarbamimidoyl)phenyl]-1,4-diazepan-1-yl]benzenecarboximidamide
  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：

  高哌嗪 、 对氟苯腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 N,N'-bis-(4-cyanophenyl)homopiperazine
  参考文献：
  名称：

  包含两个不连续柔性配体的不同构象异构体的多孔聚轮烷配位网络。

  摘要：

  制备了新的发散的高哌嗪衍生的配体N，N′-双（4-羧基苯基）-1，4-二氮杂环庚烷H 2 L，其包含能够提供多种不同的桥接几何结构的半刚性饱和杂环核。的反应ħ 2大号与DMSO乙酸锌给出了一个二维平行互穿聚轮烷结构1，其中环和杆通过弯曲形成的顺式- （当量，斧）扭船和反式- （AX，斧）捻椅构象分别。通过匹配结构1中的溶剂化金属位点之间的距离，可以得到一种相关的材料2可以制备掺入柱化的配体的反式-1,2-双（4-吡啶基）乙烯BPE。化合物2表现出相似的聚轮烷互穿模式，同时存在顺式和反式配体构象异构体，但显示出与dia Diamondoid网络有关的三维2.6 9拓扑。研究了两种材料的客体交换和气体吸附性能；尽管化合物1对客体交换显示出较差的稳定性且气体吸收可忽略不计，但较高连通性的微孔化合物2显示客体交换较容易，并且CO 2出乎意料地高在1 bar和273 K下的最大吸附容量为12 wt％，吸附的​​零负荷焓为-32

  DOI：

  10.1021/acs.inorgchem.6b01713

文献信息

• Antitumor and Anti-Pneumocystis Carinii Activities of Novel Bisbenzamidines
  作者：Jean Jacques Vanden Eynde、Annie Mayence、Melissa T. Johnson、Tien L. Huang、Margaret S. Collins、Sandra Rebholz、Peter D. Walzer、Melanie T. Cushion、Isaac O. Donkor

  DOI：10.1007/s00044-005-0130-2

  日期：2005.4

  Among a library of 17 bisbenzamidines connected with various linkers, compounds with a flexible pentanediamide (10) or hexanediamide (12) linker were the most potent derivatives against rat Pneumocystis carinii (IC50 values of 3 and 2 nM, respectively) and had the highest selectivity index ratios (GI(50) of human tumor cells/IC50 of rat P. carinii cells) of > 10(4). Seven compounds caused 50% growth inhibition (GI(50)) of tumor cells at concentrations of < 100 mu M while the remaining ten were not cytotoxic. DNA binding affinity (Delta T-m) of the tested compounds did not correlate with either their anti-P. carinii activity or cytotoxicity.
• Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine
  作者：Bin Tao、Tien L Huang、Qian Zhang、Latasha Jackson、Sherry F Queener、Isaac O Donkor

  DOI：10.1016/s0223-5234(99)80102-0

  日期：1999.6

  A series of conformationally restricted analogues of pentamidine in which the flexible central bridge has been replaced by trans-cyclopropyl, phenyl, pyridinyl, piperazinyl or homopiperazinyl groups as conformationally restricted linkers have been synthesized. The anti-Pneumocystis carinii activity of these compounds was evaluated in a cell culture model and the DNA binding affinity was determined by thermal denaturation measurements. At 1 mu M, compounds 2, 3, 5, 7, 9 and pentamidine were highly effective and caused total inhibition of P. carinii growth in culture. At 0.1 mu M, compounds 2, 5, 7 and 10 were more active than pentamidine with N, N'-bis(4-amidinophenyl)piperazine 7 being approximately 15-fold more effective than pentamidine. The most active compounds, 7 and 10, showed strong binding affinities for calf thymus DNA and poly(dA-dT); however, a clear correlation between DNA binding affinity and the in vitro anti-P. carinii activity of these compounds was not observed. The results suggest that the nature of the central Linker influences the biological actions of these compounds. (C) Elsevier, Paris.
• N,N′-Bis[4-(N-alkylamidino)phenyl]homopiperazines as anti-Pneumocystis carinii agents
  作者：Tien L Huang、Bin Tao、Yvonne Quarshie、Sherry F Queener、Isaac O Donkor

  DOI：10.1016/s0960-894x(01)00541-8

  日期：2001.10

  The synthesis, anti-Pneumocystis carinii activity and DNA binding properties of eight new N,N'-bis[4-(N-alkylamidino)phenyl]homopiperazines are reported. Compounds 2 and 8 were the most potent and caused about 70% inhibition of Pneumocystis carinii growth in a cell culture model at 1 muM concentrations. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Porous Polyrotaxane Coordination Networks Containing Two Distinct Conformers of a Discontinuously Flexible Ligand
  作者：Chris S. Hawes、Gregory P. Knowles、Alan L. Chaffee、Keith F. White、Brendan F. Abrahams、Stuart R. Batten、David R. Turner

  DOI：10.1021/acs.inorgchem.6b01713

  日期：2016.10.17

  of 1, a related material 2 can be prepared incorporating the pillaring ligand trans-1,2-bis(4-pyridyl)ethylene bpe. Compound 2 displays a similar polyrotaxane interpenetration mode, permitted by the presence of both cis and trans ligand conformers, but displays a three-dimensional 2.69 topology related to the dia diamondoid network. The guest exchange and gas adsorption properties of both materials were

  制备了新的发散的高哌嗪衍生的配体N，N′-双（4-羧基苯基）-1，4-二氮杂环庚烷H 2 L，其包含能够提供多种不同的桥接几何结构的半刚性饱和杂环核。的反应ħ 2大号与DMSO乙酸锌给出了一个二维平行互穿聚轮烷结构1，其中环和杆通过弯曲形成的顺式- （当量，斧）扭船和反式- （AX，斧）捻椅构象分别。通过匹配结构1中的溶剂化金属位点之间的距离，可以得到一种相关的材料2可以制备掺入柱化的配体的反式-1,2-双（4-吡啶基）乙烯BPE。化合物2表现出相似的聚轮烷互穿模式，同时存在顺式和反式配体构象异构体，但显示出与dia Diamondoid网络有关的三维2.6 9拓扑。研究了两种材料的客体交换和气体吸附性能；尽管化合物1对客体交换显示出较差的稳定性且气体吸收可忽略不计，但较高连通性的微孔化合物2显示客体交换较容易，并且CO 2出乎意料地高在1 bar和273 K下的最大吸附容量为12 wt％，吸附的​​零负荷焓为-32
• 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.