N-tetradecylpyrimidin-2-amine | 1261077-02-4

• 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-tetradecylpyrimidin-2-amine
• CAS: 1261077-02-4
• 化学式: C₁₈H₃₃N₃
• 分子量: 291.48
• InChiKey: RYARTMBYFHLMSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tetradecylpyrimidin-2-amine 在 4-二甲氨基吡啶 、 磷酸 、 一水合肼 作用下， 以 水 、 乙腈 为溶剂， 反应 5.25h， 生成 5-phenyl-1-tetradecyl-1H-imidazol-2-amine
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148
• 作为产物：
  描述：

  2-氯嘧啶 、 十四胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 以88%的产率得到N-tetradecylpyrimidin-2-amine
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148

文献信息

• Structure–activity relationship of 2-hydroxy-2-aryl-2,3-dihydro-imidazo[1,2-a]pyrimidinium salts and 2N-substituted 4(5)-aryl-2-amino-1H-imidazoles as inhibitors of biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa
  作者：Hans P.L. Steenackers、Denis S. Ermolat’ev、Bharat Savaliya、Ami De Weerdt、David De Coster、Anamik Shah、Erik V. Van der Eycken、Dirk E. De Vos、Jozef Vanderleyden、Sigrid C.J. De Keersmaecker

  DOI：10.1016/j.bmc.2011.04.026

  日期：2011.6

  general prevented the biofilm formation of both species at low micromolar concentrations, while salts with a shorter n-alkyl or cyclo-alkyl chain (C1–C5) or longer n-alkyl chain (C11–C14) were much less potent. Salts with a long cyclo-alkyl chain however were found to be strong biofilm inhibitors. Furthermore, we demonstrated the biofilm inhibitory potential of salts with certain aromatic substituents

  80个1取代的2-羟基-2-芳基-2,3-二氢咪唑并[1,2- a ]嘧啶盐和54 2 N取代的4（5）-芳基-2-氨基-1 H的文库合成了咪唑并测试了鼠伤寒沙门氏菌和铜绿假单胞菌对生物膜形成的拮抗作用。发现在盐的1-位上的取代基的性质对其生物膜抑制活性具有重大影响。一般而言，在1位取代的具有中等长度正烷基或环烷基链（C7–C10）的盐通常会阻止两种物种在低摩尔浓度下的生物膜形成，而具有较短n-烷基或环烷基链（C1-C5）或更长的正烷基链（C11-C14）效力较弱。然而，发现具有长环烷基链的盐是强生物膜抑制剂。此外，我们证明了在1位具有某些芳族取代基的盐（例如胡椒基或3-甲氧基苯乙炔基）的生物膜抑制潜力。发现2-氨基咪唑的活性取决于2 N-取代基的性质。与未取代的对应物相比，在2 N位具有正丁基，异丁基，正戊基，环戊基或正己基链的化合物具有更高的活性，而具有2 N较短的化合物-烷基链确实具有降低的活性，而具有更长的2
• Structure−Activity Relationship of 4(5)-Aryl-2-amino-1<i>H</i>-imidazoles, <i>N</i>1-Substituted 2-Aminoimidazoles and Imidazo[1,2-<i>a</i>]pyrimidinium Salts as Inhibitors of Biofilm Formation by <i>Salmonella</i> Typhimurium and <i>Pseudomonas aeruginosa</i>
  作者：Hans P. L. Steenackers、Denis S. Ermolat’ev、Bharat Savaliya、Ami De Weerdt、David De Coster、Anamik Shah、Erik V. Van der Eycken、Dirk E. De Vos、Jozef Vanderleyden、Sigrid C. J. De Keersmaecker

  DOI：10.1021/jm1011148

  日期：2011.1.27

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.