2-cyano-N-(4-cyano-1-(4-cyanophenyl)-1H-imidazol-5-yl)acetamide | 1395082-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-cyano-N-(4-cyano-1-(4-cyanophenyl)-1H-imidazol-5-yl)acetamide
• 英文别名: 2-cyano-N-[5-cyano-3-(4-cyanophenyl)imidazol-4-yl]acetamide
• CAS: 1395082-81-1
• 化学式: C₁₄H₈N₆O
• 分子量: 276.257
• InChiKey: XJBQPKYKTZHEGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(4-cyano-1-(4-cyanophenyl)-1H-imidazol-5-yl)acetamide 、 邻香草醛 在 sodium carbonate 作用下， 以 水 为溶剂， 以86%的产率得到N-(4-cyano-1-(4-cyanophenyl)-1H-imidazol-5-yl)-2-imino-8-methoxy-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships

  摘要：

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.009
• 作为产物：
  描述：

  氰乙酸 、 5-amino-1-(4-cyanophenyl)-1H-imidazole-4-carbonitrile 在 乙酸酐 作用下， 以67%的产率得到2-cyano-N-(4-cyano-1-(4-cyanophenyl)-1H-imidazol-5-yl)acetamide
  参考文献：
  名称：

  New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships

  摘要：

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.009

文献信息

• New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships
  作者：Filipe Areias、Marta Costa、Marián Castro、José Brea、Elisabet Gregori-Puigjané、M. Fernanda Proença、Jordi Mestres、María I. Loza

  DOI：10.1016/j.ejmech.2012.05.009

  日期：2012.8

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.