N,N'-bis(2-pyrimidyl)-1,4-tetramethylenediamine | 872601-35-9

• 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)-1,4-tetramethylenediamine
• 英文别名: N,N'-bis(2-pyrimidyl)tetramethylenediamine；N,N'-di(pyrimidin-2-yl)butane-1,4-diamine
• CAS: 872601-35-9
• 化学式: C₁₂H₁₆N₆
• 分子量: 244.299
• InChiKey: IHTDVAQULKLMEH-UHFFFAOYSA-N

物化性质

• 沸点：
  473.7±55.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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)-1,4-tetramethylenediamine 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 、 四亚甲基二胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以70%的产率得到N,N'-bis(2-pyrimidyl)-1,4-tetramethylenediamine
  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

• A Combined Experimental and Theoretical Study of Anion–π Interactions in Bis(pyr­imidine) Salts
  作者：Angel Garcia-Raso、Francisca M. Albertí、Juan J. Fiol、Andrés Tasada、Miquel Barceló-Oliver、Elies Molins、Daniel Escudero、Antonio Frontera、David Quiñonero、Pere M. Deyà

  DOI：10.1002/ejoc.200700809

  日期：2007.12

  dinium) tetrafluoroborate salt that exhibits anion–π interactions that are responsible for the crystal packing. The anion forms a sandwich complex with two pyrimidine rings. When the anion is nitrate, the crystal packing is governed by anion–π interactions and hydrogen bonds, and the sandwich complex is not formed. Finally, a theoretical study of the anion–π interactions in charged pyrimidine rings

  我们报告了 N,N'-四亚甲基双（2-氨基嘧啶鎓）四氟硼酸盐的合成和 X 射线表征，该盐表现出导致晶体堆积的阴离子-π 相互作用。阴离子与两个嘧啶环形成夹心复合物。当阴离子为硝酸根时，晶体堆积受阴离子-π相互作用和氢键控制，不会形成夹心复合物。最后，对带电嘧啶环中阴离子-π 相互作用的理论研究与实验结果非常一致。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• 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.
• 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。