N-(2',4'-dichlorobenzyl)-2-cyanoacetamide | 64488-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2',4'-dichlorobenzyl)-2-cyanoacetamide
• 英文别名: 2-cyano-N-[(2,4-dichlorophenyl)methyl]acetamide
• CAS: 64488-09-1
• 化学式: C₁₀H₈Cl₂N₂O
• 分子量: 243.092
• InChiKey: VQNFQLSOKIRCCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2',4'-dichlorobenzyl)-2-cyanoacetamide 、 2-氨基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以78%的产率得到2-Amino-N-(2,4-dichlorobenzyl)quinoline-3-carboxamide
  参考文献：
  名称：

  Cyanoacetamides (IV): Versatile One-Pot Route to 2-Quinoline-3-carboxamides

  摘要：

  Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlander reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

  DOI：

  10.1021/co3000133
• 作为产物：
  描述：

  氰乙酸甲酯 、 2,4-二氯苯甲胺 生成 N-(2',4'-dichlorobenzyl)-2-cyanoacetamide
  参考文献：
  名称：

  Cyanoacetamides (IV): Versatile One-Pot Route to 2-Quinoline-3-carboxamides

  摘要：

  Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlander reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

  DOI：

  10.1021/co3000133

文献信息

• Modulators of LXR
  申请人：——

  公开号：US20030181420A1

  公开（公告）日：2003-09-25

  Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of nuclear receptors, including liver X receptor (LXR) and orphan nuclear receptors. In certain embodiments, the compounds are N-substituted pyridones.

  提供了用于调节核受体活性的化合物、组合物和方法。具体来说，提供了用于调节核受体活性的杂环化合物，包括肝X受体（LXR）和孤儿核受体。在某些实施方式中，这些化合物是N-取代吡啶酮。
• Impact of an aryl bulky group on a one-pot reaction of aldehyde with malononitrile and <i>N</i>-substituted 2-cyanoacetamide
  作者：Ruturajsinh M. Vala、Divyang M. Patel、Mayank G. Sharma、Hitendra M. Patel

  DOI：10.1039/c9ra05975j

  日期：——

  In this study, we successfully explored the effect of steric hindrance on the one-pot reaction of different aryl aldehydes with malononitrile and N-substituted 2-cyanoacetamide in the presence of piperidinium acetate as the catalyst. It involved the Knoevenagel condensation of the aldehyde and malononitrile to produce arylidene malononitrile as an intermediate, which was further treated with N-substituted

  在这项研究中，我们成功地探索了空间位阻对不同芳基醛与丙二腈和N-取代的 2-氰基乙酰胺在乙酸哌啶鎓作为催化剂存在下的一锅反应的影响。它涉及醛和丙二腈的 Knoevenagel 缩合生成亚芳基丙二腈作为中间体，当空间体积较小时，进一步用N-取代的 2-氰基乙酰胺处理得到 6-氨基-2-吡啶酮-3,5-二甲腈衍生物组参与。高位阻改变了较早的反应路线，并通过较慢的路线产生了N-取代的2-氰基丙烯酰胺。
• [EN] NOVEL ARGINASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS D'ARGINASE
  申请人：UNIV GRONINGEN

  公开号：WO2020249821A1

  公开（公告）日：2020-12-17

  The present invention relates to novel arginase inhibitors of formula (I). These novel compounds are useful in the treatment of diseases that are associated with arginase activity, such as asthma, allergic rhinitis and COPD (chronic obstructive pulmonary disease).

  本发明涉及式(I)的新型精氨酸酶抑制剂。这些新型化合物在治疗与精氨酸酶活性相关的疾病方面具有用途，如哮喘、过敏性鼻炎和慢性阻塞性肺疾病（COPD）。
• One-pot two-step catalytic synthesis of 6-amino-2-pyridone-3,5-dicarbonitriles enabling anti-cancer bioactivity
  作者：Lynden G. Nicely、Ruturajsinh M. Vala、Dipti B. Upadhyay、Joaquina Nogales、Celestine Chi、Sourav Banerjee、Hitendra M. Patel

  DOI：10.1039/d2ra03579k

  日期：——

  glioblastoma cell lines. Furthermore, 5o in combination with specific clinically relevant small molecule inhibitors induced enhanced cytotoxicity in glioblastoma cells. Through our current work, we establish a promising 6-amino-2-pyridone-3,5-dicarbonitrile based lead compound with anti-cancer activity either on its own or in combination with specific clinically relevant small molecule kinase and proteasome

  我们报告了使用天然产物催化剂甜菜碱和碳酸胍的生物活性 6-氨基-2-吡啶酮-3,5-二甲腈衍生物的一锅两步合成。在 16 种衍生物库中的特定分子中观察到抗癌生物活性。在这些化合物中，5o对胶质母细胞瘤细胞具有最有效的抗癌活性，并被选为进一步研究。化合物5o对肝癌、乳腺癌、肺癌以及原发性患者来源的胶质母细胞瘤细胞系显示出抗癌特性。此外，5o与特定的临床相关小分子抑制剂联合使用可增强胶质母细胞瘤细胞的细胞毒性。通过我们目前的工作，我们建立了一种有前景的基于 6-氨基-2-吡啶酮-3,5-二甲腈的先导化合物，其本身或与特定的临床相关小分子激酶和蛋白酶体抑制剂组合具有抗癌活性。
• US4028084A
  申请人：——

  公开号：US4028084A

  公开（公告）日：1977-06-07