2-amino-4-[4-(dimethylamino)phenyl]-6-phenyl-pyridine-3-carbonitrile | 573937-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-[4-(dimethylamino)phenyl]-6-phenyl-pyridine-3-carbonitrile
• 英文别名: 2-amino-4-[4-(dimethylamino)phenyl]-6-phenyl-3-pyridinecarbonitrile；2-Amino-4-[4-(dimethylamino)phenyl]-6-phenylpyridine-3-carbonitrile
• CAS: 573937-42-5
• 化学式: C₂₀H₁₈N₄
• 分子量: 314.39
• InChiKey: MEWHRMNNCJSQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈 、 苯乙酮 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-amino-4-[4-(dimethylamino)phenyl]-6-phenyl-pyridine-3-carbonitrile
  参考文献：
  名称：

  2-Amino-6-furan-2-yl-4-substituted Nicotinonitriles as A_2A Adenosine Receptor Antagonists

  摘要：

  A2A adenosine receptor antagonists usually have bi- or tricyclic N aromatic systems with varying substitution patterns to achieve desired receptor affinity and selectivity. Using a pharmacophore model designed by overlap of nonxanthine type of previously known A2A antagonists, we synthesized a new class of compounds having a 2-amino nicotinonitrile core moiety. From our data, we conclude that the presence of at least one furan group rather than phenyl is beneficial for high affinity on the A2A adenosine receptor. Compounds 39 (LUF6050) and 44 (LUF6080) of the series had Ki values of 1.4 and 1.0 nM, respectively, with reasonable selectivity toward the other adenosine receptor subtypes, A,, A2B, and A3. The high affinity of 44 was corroborated in a cAMP second messenger assay, yielding subnanomolar potency for this compound.

  DOI：

  10.1021/jm701594y

文献信息

• Facile microwave-assisted preparation of an ester-based cationic gemini surfactant for the improved micellar synthesis of aminocyanopyridines
  作者：Fatemeh Tamaddon、Seyd-Ehsan Tadayonfar

  DOI：10.1016/j.molstruc.2020.127728

  日期：2020.5

  Abstract In this work, a diester cationic gemini surfactant (DCGS) was prepared from the reaction of N,N-dimethyldodecylamine with the microwave (MW)-assisted synthesized spacer ethane-1,2-diyl bis(2-chloroacetate) (EDBC) by the three-component reaction of ethylene glycol with chloroacetic acid (2 equiv.) under MW-irradiation. The structure of the spacer EDBC and surfactant DCGS were evaluated by 1H NMR

  摘要 在这项工作中，通过 N,N-二甲基十二胺与微波辅助合成的间隔基乙烷-1,2-二(2-氯乙酸)(EDBC) 反应制备了二酯阳离子双子表面活性剂 (DCGS)。通过乙二醇与氯乙酸（2 当量）在 MW 辐射下的三组分反应。间隔物 EDBC 和表面活性剂 DCGS 的结构通过 1H NMR、FT-IR、熔点、表面张力 (γ)、悬滴和临界胶束浓度 (CMC) 分析以及 DCGS 的可裂解性测试进行评估。DCGS 的 γ 和 CMC 为 36.8（~50% γ H2O）和 1.62 × 10-5 mol L-1，低于简单的 GS。通过苯乙酮、丙二腈、(NH4)2CO3 和醛在水中的四组分反应，评估了 DCGS 在合成氨基氰基吡啶中的催化性能。热稳定性，
• 2-Amino-6-furan-2-yl-4-substituted Nicotinonitriles as A_2A Adenosine Receptor Antagonists
  作者：Monica Mantri、Olivier de Graaf、Jacobus van Veldhoven、Anikó Göblyös、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Regina Link、Henk de Vries、Margot W. Beukers、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm701594y

  日期：2008.8.1

  A2A adenosine receptor antagonists usually have bi- or tricyclic N aromatic systems with varying substitution patterns to achieve desired receptor affinity and selectivity. Using a pharmacophore model designed by overlap of nonxanthine type of previously known A2A antagonists, we synthesized a new class of compounds having a 2-amino nicotinonitrile core moiety. From our data, we conclude that the presence of at least one furan group rather than phenyl is beneficial for high affinity on the A2A adenosine receptor. Compounds 39 (LUF6050) and 44 (LUF6080) of the series had Ki values of 1.4 and 1.0 nM, respectively, with reasonable selectivity toward the other adenosine receptor subtypes, A,, A2B, and A3. The high affinity of 44 was corroborated in a cAMP second messenger assay, yielding subnanomolar potency for this compound.