N,N'-bis(4-cyanophenyl)-2,6-pyridinediamide | 250343-09-0

• 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)-2,6-pyridinediamide
• 英文别名: 2-N,6-N-bis(4-cyanophenyl)pyridine-2,6-dicarboxamide
• CAS: 250343-09-0
• 化学式: C₂₁H₁₃N₅O₂
• 分子量: 367.367
• InChiKey: CPDTVIDMVJEWHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-cyanophenyl)-2,6-pyridinediamide 在 盐酸 、 氨 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 Pyridine-2,6-dicarboxylic acid bis-[(4-carbamimidoyl-phenyl)-amide]
  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：

  2,6-氯甲酰吡啶 、 对氨基苯腈 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 N,N'-bis(4-cyanophenyl)-2,6-pyridinediamide
  参考文献：
  名称：

  Dianilides of dipicolinic acid function as synthetic chloride channels

  摘要：

  我们报告说，N2,N6-双（4-硝基苯基）吡啶-2,6-二甲酰胺与已知的间苯二甲酸二酰二胺相关，可通过磷脂双层膜转运 Cl- 离子，并显示出明确的通道活性证据。

  DOI：

  10.1039/b924812a

文献信息

• 10.1039/d4nj01330a
  作者：Bracken, Matthew L.、Fernandes, Manuel A.、Wamwangi, Daniel、Munro, Orde Q.

  DOI：10.1039/d4nj01330a

  日期：——

  NNN bis-aryl amide pincer ligands may be designed to meet the structural requirements for Cu(II) metallocycle hexamer formation, giving supramolecular crystals containing solvent-accesible voids.

  NNN双芳基酰胺钳配体可被设计来满足Cu( II )金属环六聚体形成的结构要求，从而得到含有溶剂可进入的空隙的超分子晶体。
• 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.
• Anion Complexation and Transport by Isophthalamide and Dipicolinamide Derivatives: DNA Plasmid Transformation in <i>E. coli</i>
  作者：Jason L. Atkins、Mohit B. Patel、Megan M. Daschbach、Joseph W. Meisel、George W. Gokel

  DOI：10.1021/ja304816e

  日期：2012.8.22

  Tris-arenes based on either isophthalic acid or 2,6-dipicolinic acid have been known for more than a decade to bind anions. Recent studies have also demonstrated their ability to transport various ions through membranes. In this report, we demonstrate two important properties of these simple diamides. First, they transport plasmid DNA into Escherichia colt about 2-fold over controls, where the ampicillin resistance gene is expressed in the bacteria. These studies were done with plasrnid DNA (similar to 2.6 kilobase (kb)) in JM109 E. coli cells. Second, known methods do not typically transport large plasmids (>15 kb). We demonstrate here that transformation of large pVIB plasmids (i.e., >20 kb) were enhanced over water controls by similar to 10-fold. These results are in striking contrast to the normal decrease in transformation with increasing plasmid size.
• 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.
• Dianilides of dipicolinic acid function as synthetic chloride channels
  作者：Carl R. Yamnitz、Saeedeh Negin、I. Alexandru Carasel、Rudolph K. Winter、George W. Gokel

  DOI：10.1039/b924812a

  日期：——

  We report that N2,N6-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide, which is related to known isophthalic acid dianilides, transports Cl− ions through phospholipid bilayer membranes and shows clear evidence of channel activity.

  我们报告说，N2,N6-双（4-硝基苯基）吡啶-2,6-二甲酰胺与已知的间苯二甲酸二酰二胺相关，可通过磷脂双层膜转运 Cl- 离子，并显示出明确的通道活性证据。