2-(戊基氨基)嘧啶 | 14095-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-(戊基氨基)嘧啶
• 英文名称: 2-(pentylamino)pyrimidine
• 英文别名: N-pentylpyrimidin-2-amine；2-Amylamino-pyrimidin；2-Pentylamino-pyrimidin；pentyl-pyrimidin-2-yl-amine；Pyrimidine, 2-n-pentylamino-
• CAS: 14095-75-1
• 化学式: C₉H₁₅N₃
• mdl: MFCD11125712
• 分子量: 165.238
• InChiKey: LZKJSMXFCLJVEL-UHFFFAOYSA-N

物化性质

• 沸点：
  277.5±23.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 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：

  2-(戊基氨基)嘧啶 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-(4-chlorophenyl)-1-pentyl-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 、 1-氨基戊烷 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以75%的产率得到2-(戊基氨基)嘧啶
  参考文献：
  名称：

  Identification of a Human Toll-Like Receptor (TLR) 8-Specific Agonist and a Functional Pan-TLR Inhibitor in 2-Aminoimidazoles

  摘要：

  Activation of human toll-like receptor-8 (TLR8), expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells, evokes a distinct cytokine profile which favors the development of Type 1 helper T cells. Part structures of the 2-aminobenzimidazole scaffold were examined with a-view to identifying structural requisites corresponding to the smallest possible fragment of the benzimidazole core that would allow for retention of TLR8-agonistic activity. TLR8-specific agonistic activity was retained in 1-penty1-4-phenyl-1H-imidazol-2-amine. The crystal structure of this compound bound to the TLR8 ectodomain displayed binding interactions that are common to other TLR8 agonists. This compound showed markedly attenuated proinflammatory properties in ex vivo human blood models. SAP. studies revealed that 4-(2-(benzyloxy)pheny1)-1-pentyl-1H-imidazol-2-amine inhibited TLR signaling in a variety of TLR reporter cell lines, as well as in pharmacologically relevant human blood model systems. A kinase screen of this compound showed relative specificity for calmodulin kinases.

  DOI：

  10.1021/acs.jmedchem.6b00023

文献信息

• [EN] PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS PYRIDINES
  申请人：ASTRAZENECA AB

  公开号：WO2009153589A1

  公开（公告）日：2009-12-23

  The present invention relates to compounds that inhibit of focal adhesion kinase function, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment in warm-blooded animals such as humans of diseases such as cancer.

  本发明涉及抑制细胞焦点粘附激酶功能的化合物，其制备方法，含有其作为活性成分的药物组合物，以及它们作为药物的用途，以及用于制造用于治疗温血动物（如人类）癌症等疾病的药物。
• NOVEL 4,6-DISUBSTITUTED AMINOPYRIMIDINE DERIVATIVES HAVING BOTH AROMATIC AND HALOGENIC SUBSTITUENTS
  申请人：Lori Franco

  公开号：US20140057911A1

  公开（公告）日：2014-02-27

  Certain 4,6-disubstituted aminopyrimidine derivatives having both aromatic and halogenic substituents.

  某些具有芳香族和卤素取代基的4,6-二取代氨基嘧啶衍生物。
• Efficient One-Pot, Two-Step, Microwave-Assisted Procedure for the Synthesis of Polysubstituted 2-Aminoimidazoles
  作者：Denis S. Ermolat'ev、Eugene V. Babaev、Erik V. Van der Eycken

  DOI：10.1021/ol062421c

  日期：2006.12.1

  A microwave-assisted, one-pot, two-step protocol was developed for the construction of polysubstituted 2-aminoimidazoles. This process involves the sequential formation of imidazo[1,2-a]pyrimidinium salts from readily available 2-aminopyrimidines and alpha-bromocarbonyl compounds, followed by opening of the pyrimidine ring with hydrazine. [reaction: see text]

  开发了微波辅助的一锅两步操作规程，用于构建多取代的2-氨基咪唑。该过程涉及由容易获得的2-氨基嘧啶和α-溴羰基化合物顺序形成咪唑并[1,2-a]嘧啶鎓盐，然后用肼打开嘧啶环。[反应：看文字]
• 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
• A preliminary investigation of Mesoionic Xanthine analogues as inhibitors of platelet aggregation
  作者：Mark Hellberg、James F. Stubbins、Richard A. Glennon

  DOI：10.1016/s0968-0896(00)00123-1

  日期：2000.8

  A series of mesoionic xanthines (e.g. mesoionic thiazolopyrimidines, 3, and thiadiazolopyrimidines, 5) and related analogues were examined as inhibitors of human platelet aggregation. Appropriately substituted compounds were found to fully inhibit platelet aggregation, and anhydro-(6-ethyl-8-isopentyl-7-oxo-5-hydroxy-1,3,4-thiadiazolo[3,2 -a]pyrimidinium hydroxide) (5b) was 40 times more potent than

  研究了一系列中离子黄嘌呤（例如，中离子噻唑并嘧啶3，和噻二唑并嘧啶5）和相关类似物作为人类血小板聚集的抑制剂。发现适当取代的化合物可完全抑制血小板凝集，并形成脱水-（6-乙基-8-异戊基-7-氧代-5-羟基-1,3,4-噻二唑[3,2-a]氢氧化嘧啶鎓）（5b ）的效力是与结构相关的黄嘌呤茶碱（1）的4​​0倍。凝胶过滤研究表明，化合物5b不可逆地抑制聚集，这可能是由于其充当潜在的酰化剂的能力。