2-amino-6-phenyl-4-(3-thienyl)-3-pyridinecarbonitrile | 1213227-24-7

• 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-6-phenyl-4-(3-thienyl)-3-pyridinecarbonitrile
• 英文别名: 2-imino-6-phenyl-4-(thiophen-3-yl)-1,2-dihydropyridine-3-carbonitrile
• CAS: 1213227-24-7
• 化学式: C₁₆H₁₁N₃S
• 分子量: 277.3
• InChiKey: LAMXJZBUJRLGFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  丙二腈 、 苯乙酮 、 3-噻吩甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以62%的产率得到2-amino-6-phenyl-4-(3-thienyl)-3-pyridinecarbonitrile
  参考文献：
  名称：

  Discovery of colon tumor cell growth inhibitory agents through a combinatorial approach

  摘要：

  Two series with the general formula of 4,6-diaryl-2-oxo-1,2 dihydropyridine-3-carbonitriles and their isosteric 4,6-diaryi-2-imino-1,2-dihydropyridine-3-carbonitrile were synthesized through one pot reaction of the appropriate acetophenone, aldehyde, ammonium acetate with ethyl cyanoacetate or malononitrile, respectively. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human HT-29 colon tumor cell line, as well as their PDE3 inhibitory activity. Compound 4-(2-Ethoxyphenyl)-2-oxo-6-thiophen-3-yl-1,2-dihydropyridine-3 carbonitrile (21) showed tumor cell growth inhibitory activity with an IC50 value of 1.25 mu M. Meanwhile, 4-(4-Ethoxyphenyl)-2-imino-6-(thiophen-3-yl)-1,2-dihydropyridine-3-carbonitrile (26) showed inhibitory effect upon PDE3 using cAMP or cGMP as substrate. No correlation exists between PDE3 inhibition and the tumor cell growth inhibitory activity. Docking compound 21 to other possible molecular targets showed the potential to bind PIM1 Kinase. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.029

文献信息

• Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation
  作者：Chandra Sekhar Challa、Naresh Kumar Katari、Varadacharyulu Nallanchakravarthula、Devanna Nayakanti、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1016/j.molstruc.2021.130541

  日期：2021.9

  The 2-amino nicotinonitrile framework has been explored first time for the identification of potential inhibitors of SIRT1. Thus a series of targeted 2-amino-4,6-disubstituted nicotinonitrile derivatives were synthesized by employing an ultrasound assisted MCR of ketones, aldehydes, malononitrile and ammonium acetate. The MCR was carried out in the presence of Amberlyst-15 in MeCN under mild conditions

  首次探索了2-氨基烟腈框架，以鉴定SIRT1的潜在抑制剂。因此，通过使用酮，醛，丙二腈和乙酸铵的超声辅助MCR，合成了一系列靶向的2-氨基-4,6-二取代烟腈衍生物。在温和的条件下在MeCN中Amberlyst-15的存在下进行MCR，以高收率得到所需的产物。在没有空气的情况下，反应效率较低，而Amberlyst-15，超声，空气和MeCN的组合对于该MCR的成功至关重要。在体外测试SIRT1抑制潜能时，几种合成的化合物表现出良好的活性，其中5c，5e和5n被确定为最有效的（IC 50〜3μM）和比已知的抑制剂的烟酰胺（IC更好50〜109微米）。在计算机对接研究中，这三种化合物显示出比烟酰胺更好的结合能（> 100 kcal / mol）和更高的相互作用数（结合能为-88.38 kcal / mol）。烟腈衍生物的氨基（–NH 2）和氰基（–CN）分别与ASN346和HIS363残基形成H键，烟酰胺通过其酰胺（–CONH
• Graphene oxide: a reusable and metal-free carbocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridines in water
  作者：Dariush Khalili

  DOI：10.1016/j.tetlet.2016.03.020

  日期：2016.4

  A one-pot synthesis of 2-amino-3-cyanopyridine derivatives has been demonstrated through the multicomponent reaction of aldehydes, ketones, malononitrile, and ammonium acetate using graphene oxide as a heterogeneous catalyst in water as a green medium. The graphene oxide catalyst is very mild, effective, and most of its activity is preserved after being reused for five times.

  已经通过醛，酮，丙二腈和乙酸铵的多组分反应，使用氧化石墨烯作为非均相催化剂，在水中作为绿色介质，通过一锅法合成了2-氨基-3-氰基吡啶衍生物。氧化石墨烯催化剂非常温和，有效，在重复使用五次后，大部分活性得以保留。
• Highly efficient four-component synthesis of 2-amino-3-cyanopyridines using doped nano-sized copper(I) oxide (Cu₂O) on melamine–formaldehyde resin
  作者：Somayeh Behrouz

  DOI：10.3184/174751916x14709292404728

  日期：2016.9

  A convenient and facile four-component synthesis is described of 2-amino-3-cyanopyridine derivatives from readily available starting materials catalysed by doped nano-sized Cu2O on melamine–formaldehyde resin (nano-Cu2O–MFR). In this method, treatment of different aldehydes, ketones, malononitrile, and ammonium acetate in refluxing H2O/EtOH (1:1) in the presence of doped nano-Cu2O–MFR as a highly efficient

  描述了一种方便且简便的四组分合成方法，该合成方法来自易于获得的起始材料，由三聚氰胺-甲醛树脂（纳米-Cu2O-MFR）上掺杂的纳米级 催化，合成 2-氨基-3-氰基吡啶衍生物。在该方法中，在作为高效多相催化剂的掺杂纳米 -MFR 存在下，在回流 H2O/EtOH (1:1) 中处理不同的醛、酮、丙二腈和醋酸铵，得到相应的 2-amino-3 -氰基吡啶的产率非常好。纳米 -MFR 是一种廉价且稳定的纳米催化剂，可以很容易地回收并重复使用许多连续的反应运行，而不会显着降低其活性。
• Catalyst-free three-component synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles under solvent-free conditions
  作者：Mohammad Hosein Sayahi、Seyyed Jafar Saghanezhad、Mohammad Mahdavi

  DOI：10.1007/s10593-019-02527-0

  日期：2019.8

  A novel efficient one-pot synthesis of 2-amino-4,6-diarylpyridine-3-carbonitriles is described. Method involves heating the mixture of an acetophenone oxime, aldehyde, and malononitrile without any catalyst under solvent-free conditions to give the title compounds in good to high yields.

  描述了2-氨基-4,6-二芳基吡啶-3-腈的新型有效的一锅合成。该方法涉及在无溶剂条件下，在无催化剂的情况下加热苯乙酮​​肟，醛和丙二腈的混合物，以高至高收率得到标题化合物。
• Four-Component Synthesis of 2-Amino-3-Cyanopyridine Derivatives Catalyzed by Cu@imineZCMNPs as a Novel, Efficient and Simple Nanocatalyst Under Solvent-Free Conditions
  作者：Asieh Yahyazadeh、Esmayeel Abbaspour-Gilandeh、Mehraneh Aghaei-Hashjin

  DOI：10.1007/s10562-018-2318-3

  日期：2018.4

  was investigated for synthesis of 2-amino-3-cyanopyridine derivatives via a one-pot four-component reaction of various types of aldehydes, acetophenone, malononitrile, and ammonium acetate in the presence of 10 mg Cu@imineZCMNPs catalyst. The favorable products were achieved with high quantitative yields and easy isolation of products in short reaction times under solvent-free conditions. The prepared

  在10 mg Cu@imineZCMNPs催化剂存在下，通过各种醛类、苯乙酮、丙二腈和乙酸铵的一锅四组分反应，研究了一种高效便捷的合成2-氨基-3-氰基吡啶衍生物的方法. 在无溶剂条件下，在较短的反应时间内以高定量收率和易于分离的方式获得了有利的产品。通过傅里叶变换红外光谱、能量色散X射线、热重分析、X射线衍射、透射电子显微镜、扫描电子显微镜和振动样品磁强计对制备的催化体系进行了表征。由于催化剂的磁性，它可以很容易地通过外部磁场回收并重复使用。图形摘要