2-amino-4-phenyl-6-(thiophen-2-yl)nicotinonitrile | 120239-01-2

• 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-phenyl-6-(thiophen-2-yl)nicotinonitrile
• 英文别名: 2-amino-4-phenyl-6-thiophen-2-yl-nicotinonitrile；2-amino-4-phenyl-6-thiophen-2-ylpyridine-3-carbonitrile
• CAS: 120239-01-2
• 化学式: C₁₆H₁₁N₃S
• 分子量: 277.349
• InChiKey: CMOAUWPKTBSUQT-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(1-苯基亚乙基)丙二腈 在 羟胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-4-phenyl-6-(thiophen-2-yl)nicotinonitrile
  参考文献：
  名称：

  [5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a synthetic route to multi-substituted 2-aminopyridines

  摘要：

  开发了一种简便且高效的合成多取代2-氨基吡啶的方法，通过在非常温和的条件下，将易于获得的2,4-戊二烯腈与羟胺（NH2OH）进行形式上的[5C + 1N]环化反应，涉及连续的分子间氮亲核加成、分子内氮环化和脱水反应。

  DOI：

  10.1039/c2ob27053f

文献信息

• Apoptosis: A target for anticancer therapy with novel cyanopyridines
  作者：Magda M.F. Ismail、Amel M. Farrag、Marwa F. Harras、Mona H. Ibrahim、Ahmed B.M. Mehany

  DOI：10.1016/j.bioorg.2019.103481

  日期：2020.1

  growth of cancer cells. So, aiming the apoptotic pathway is an exciting approach to finding new anticancer agents. A novel series of cyanopyridines was designed and synthesized for antiproliferative evaluation. 2-Amino-6-(4-(benzyloxy)phenyl)-4-(4-(dimethylamino)phenyl) nicotinonitrile 10f was the most potent inhibitor against the growth of PC-3, and HepG-2 cancer cell lines with IC50 values of 2.04

  治疗癌症的许多方法之一是终止癌细胞的不受控制的生长。因此，针对凋亡途径是寻找新的抗癌药物的令人兴奋的方法。设计并合成了一系列新的氰基吡啶，用于抗增殖评价。2-氨基-6-（4-（苄氧基）苯基）-4-（4-（二甲基氨基）苯基）烟腈10f是抑制PC-3和HepG-2癌细胞生长的最有效抑制剂，IC50值为2.04uM（选择性指数，SI分别为78.63、43）。同样，10f对正常人二倍体肺成纤维细胞系（WI-38）的生长是安全的，IC50值为160.04 uM。它的类似物10b，10d，10g和11b对PC-3和HepG-2的生长也具有活性，而对MCF-7细胞系具有抑制作用，与参考标准5-FU相比，它们显示出良好的细胞毒活性。值得注意的是，机理研究表明，与对照相比，化合物10b，10d，10f，10g和11b刺激了活性胱天蛋白酶3的水平，并使BAX / BCL2的比例提高了20-95倍。我们的结果还
• Method of using aminocyanopyridine compounds as mitogen activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Pharmacia Corporation

  公开号：US20040127519A1

  公开（公告）日：2004-07-01

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject an anminocyanopyridine MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种抑制需要抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者给予一种抑制MK-2的氨基氰基吡啶化合物或其药学上可接受的盐。
• Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase-2
  申请人：Pharmacia Corporation

  公开号：US20040142978A1

  公开（公告）日：2004-07-22

  Aminocyanopyridine compounds are described which can inhibit mitogen activated protein kinase-activated protein kinase-2. Pharmaceutical compositions and kits that contain these compounds are also described.

  描述了可抑制丝裂原活化蛋白激酶-活化蛋白激酶-2 的氨基氰吡啶化合物。还描述了含有这些化合物的药物组合物和试剂盒。
• Divergent Syntheses of 2-Aminonicotinonitriles and Pyrazolines by Copper-Catalyzed Cyclization of Oxime Ester
  作者：Qifan Wu、Yan Zhang、Sunliang Cui

  DOI：10.1021/ol500094w

  日期：2014.3.7

  Copper-catalyzed cyclization of an oxime ester toward divergent heterocycle synthesis is reported. Oxime ester serves as an enamine precursor to cyclize with malononitrile and aldehydes for access to 2-aminonicotinonitriles in a one-pot reaction, while cyclizing with N-sulfonylimines leads to synthesis of pyrazolines.
• 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.