N,N'-bis(2-pyrimidyl)-1,6-hexamethylenediamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N,N'-bis(2-pyrimidyl)-1,6-hexamethylenediamine
• 英文别名: N,N'-di(pyrimidin-2-yl)hexane-1,6-diamine
• 化学式: C₁₄H₂₀N₆
• 分子量: 272.353
• InChiKey: KNSITBRQNSQMOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-pyrimidyl)-1,6-hexamethylenediamine 在 polyphosphoric acid 作用下， 以 乙腈 为溶剂， 反应 5.25h， 生成
  参考文献：
  名称：

  Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation

  摘要：

  The increased tolerance of biofilms against disinfectants and antibiotics has stimulated research into new methods of biofilm prevention and eradication. In our previous work, we have identified the 5-aryl-2-aminoimidazole core as a scaffold that demonstrates preventive activity against biofilm formation of a broad range of bacterial and fungal species. Inspired by the dimeric nature of natural 2-aminoimidazoles of the oroidin family, we investigated the potential of dimers of our decorated 5-aryl-2-aminoimidazoles as biofilm inhibitors. A synthetic approach towards 2-aminoimidazole dimers linked by an alkyl chain was developed and a total of 48 dimers were synthesized. The linkers were introduced at two different positions, the N1-position or the N2-position, and the linker length and the substitution of the 5-phenyl ring (H, F, Cl, Br) were varied. Although, no clear correlation between linker length and biofilm inhibition was observed, a strong increase in anti-biofilm activity for almost all N1, N1'-linked dimers was obtained, compared to the respective monomers against Salmonella Typhimurium, Escherichia coli and Staphylococcus aureus. The N2, N2'-linked dimers, having a H-or F-substitution, were also found to show a strong increase in anti-biofilm activity compared to the respective monomers against these three bacterial species and against Pseudomonas aeruginosa. In addition, the obtained growth measurements suggest a broad concentration range with specific biofilm inhibition and no effect on the planktonic growth against Salmonella Typhimurium and Pseudomonas aeruginosa. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2018.01.005
• 作为产物：
  描述：

  2-氯嘧啶 、 1,6-己二胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以65%的产率得到N,N'-bis(2-pyrimidyl)-1,6-hexamethylenediamine
  参考文献：
  名称：

  Ag(i) complexes with alkylidene-bis(2-aminopyrimidines) as building units for discrete metallomacrocyclic frames. A structural and solution study

  摘要：

  烯叉双(2-氨基嘧啶)(pyr2Cx, x = 2–5)是有用的配体，能与Ag(I)生成离散的金属环。分离得到了[(pyr2C2)Ag(NO3)]2和[(H-pyr2C4)Ag(NO3)2]2的晶体结构，其中每个大环部分都通过弱相互作用与其周围环境相互作用，形成三维离散结构。另一方面，溶液研究显示，Ag(pyr2Cx)+配合物的形成平衡常数高于已知文献中单嘧啶Ag(I)配合物的值，尽管这种差异可以通过考虑Ag(I)-pyr2Cx配合物的固态结构来解释。

  DOI：

  10.1039/b508260a

文献信息

• Ag(i) complexes with alkylidene-bis(2-aminopyrimidines) as building units for discrete metallomacrocyclic frames. A structural and solution study
  作者：Angel García-Raso、Juan J. Fiol、Andrés Tasada、Francisca M. Albertí、Elies Molins、Manuel G. Basallote、María A. Máñez、María J. Fernández-Trujillo、David Sánchez

  DOI：10.1039/b508260a

  日期：——

  Alkylidene-bis(2-aminopyrimidines) (pyr2Cx, x = 2–5) are useful ligands to interact with Ag(I) yielding discrete metallocycles. Crystal structures of the [(pyr2C2)Ag(NO3)]2 and [(H-pyr2C4)Ag(NO3)2]2 have been isolated where each macrocyclic moiety interacts with their surroundings through weak interactions, yielding 3D discrete structures, On the other hand, the solution study shows that the equilibrium constants for the formation of Ag(pyr2Cx)+ complexes are higher than the literature values for Ag(I) complexes with single pyrimidines, although the differences could be explained by invoking the solid-state structures of the Ag(I)–pyr2Cx complexes.

  烯叉双(2-氨基嘧啶)(pyr2Cx, x = 2–5)是有用的配体，能与Ag(I)生成离散的金属环。分离得到了[(pyr2C2)Ag(NO3)]2和[(H-pyr2C4)Ag(NO3)2]2的晶体结构，其中每个大环部分都通过弱相互作用与其周围环境相互作用，形成三维离散结构。另一方面，溶液研究显示，Ag(pyr2Cx)+配合物的形成平衡常数高于已知文献中单嘧啶Ag(I)配合物的值，尽管这种差异可以通过考虑Ag(I)-pyr2Cx配合物的固态结构来解释。
• Synthesis, Biological Activity, and QSAR Studies of Antimicrobial Agents Containing Biguanide Isosteres
  作者：Gregory T. Wernert、David A. Winkler、George Holan、Gina Nicoletti

  DOI：10.1071/ch03146

  日期：——

  Analogues of chlorhexidine and chemically related antimicrobial compounds were synthesized, based on a model in which the bisbiguanide moieties were replaced by conformationally restricted cyclic isosteres. This model was tested by measuring the antimicrobial activities of the compounds. Quantitative structure–activity relationship (QSAR) studies showed a parabolic dependence of antimicrobial activity on the lipophilicity of the compounds. The basicity of the functional groups in the molecules was also very important, as uncharged molecules were not able to disrupt the microbial phospholipid bilayer and cause an antimicrobial effect. We compared our QSAR results to those reported in other studies of antimicrobials of diverse structure. We found very similar QSAR models for all compounds studies with a log P (octanol/water partition constant) optimum at 5.5 (neutral log P value). The form of the QSAR equations were similar, suggesting a common mode of action for these agents.

  根据双胍分子被构象受限的环状异构体取代的模型，合成了洗必泰的类似物和化学上相关的抗菌化合物。通过测定这些化合物的抗菌活性，对这一模型进行了检验。定量结构-活性关系（QSAR）研究表明，抗菌活性与化合物的亲脂性呈抛物线关系。分子中官能团的碱性也非常重要，因为不带电的分子无法破坏微生物的磷脂双分子层并产生抗菌效果。我们将我们的 QSAR 结果与其他不同结构抗菌剂的研究结果进行了比较。我们发现所有研究化合物的 QSAR 模型都非常相似，对数 P（辛醇/水分配常数）的最佳值为 5.5（中性对数 P 值）。QSAR 方程的形式相似，表明这些制剂具有共同的作用模式。
• Enhancing the anti-biofilm activity of 5-aryl-2-aminoimidazoles through nature inspired dimerisation
  作者：Tran Thi Thu Trang、Lise Dieltjens、Geert Hooyberghs、Kai Waldrant、Denis S. Ermolat'ev、Erik V. Van der Eycken、Hans P.L. Steenackers

  DOI：10.1016/j.bmc.2018.01.005

  日期：2018.5

  The increased tolerance of biofilms against disinfectants and antibiotics has stimulated research into new methods of biofilm prevention and eradication. In our previous work, we have identified the 5-aryl-2-aminoimidazole core as a scaffold that demonstrates preventive activity against biofilm formation of a broad range of bacterial and fungal species. Inspired by the dimeric nature of natural 2-aminoimidazoles of the oroidin family, we investigated the potential of dimers of our decorated 5-aryl-2-aminoimidazoles as biofilm inhibitors. A synthetic approach towards 2-aminoimidazole dimers linked by an alkyl chain was developed and a total of 48 dimers were synthesized. The linkers were introduced at two different positions, the N1-position or the N2-position, and the linker length and the substitution of the 5-phenyl ring (H, F, Cl, Br) were varied. Although, no clear correlation between linker length and biofilm inhibition was observed, a strong increase in anti-biofilm activity for almost all N1, N1'-linked dimers was obtained, compared to the respective monomers against Salmonella Typhimurium, Escherichia coli and Staphylococcus aureus. The N2, N2'-linked dimers, having a H-or F-substitution, were also found to show a strong increase in anti-biofilm activity compared to the respective monomers against these three bacterial species and against Pseudomonas aeruginosa. In addition, the obtained growth measurements suggest a broad concentration range with specific biofilm inhibition and no effect on the planktonic growth against Salmonella Typhimurium and Pseudomonas aeruginosa. (C) 2018 Published by Elsevier Ltd.