N-Cyanoacetylglycine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Cyanoacetylglycine
• 英文别名: 2-[(2-Cyanoacetyl)amino]acetic acid
• 化学式: C₅H₆N₂O₃
• mdl: MFCD19225398
• 分子量: 142.114
• InChiKey: URJSUWWPQFTYCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  水杨醛 、 N-Cyanoacetylglycine 在 sodium carbonate 、 盐酸 作用下， 以 水 为溶剂， 反应 17.5h， 生成 [(2-oxo-2H-chromene-3-carbonyl)-amino]-acetic acid
  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：

  聚甘氨酸 、 氰乙酸甲酯 在 4-二甲氨基吡啶 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N-Cyanoacetylglycine
  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

• Amino Acid Derivatives in Organic Synthesis, Part 4 [1]: Facile Synthesis of Heterocycles Containing a Glycine Residue
  作者：Laila M. Chabaka、Yehia A. Allam、Galal A. M. Nawwar

  DOI：10.1515/znb-2000-0117

  日期：2000.1.1

  Pyridines, thiazolopyridines and pyrazolopyrans containing glycinate residue were prepared by reacting N-cyanoacryloglycinate ylidenes with active methylene compounds via a Michael addition - intracyclization synthetic pathway.

  Simple routes for the synthesis of heterocycles with an amino acid residue were previously reported [1-3] as the incorportation of these residues improves the pharmacokinetics and toxicity of active compounds [4,5]. However, trials to deesterify these residues for coupling purposes were unsuccessful. So, we tried herein new approaches for synthesizing heterocyles carrying one or two glycine moieties with free carboxylic acid group to facilitate further peptide linkage [6] on one hand and on the other one could be able to form metal chelates, a property having a significant output on the toxicological behaviour [7]

  通过将N-氰基丙烯酸甘氨酸酯伊利丹与活性亚甲基化合物反应，通过Michael加成-分子内环化合成途径制备了含有甘氨酸残基的吡啶、噻唑吡啶和吡唑吡喃类化合物。以前曾报道合成带有氨基酸残基的杂环化合物的简单途径，因为这些残基的加入改善了活性化合物的药代动力学和毒性。然而，试图去酯化这些残基以进行偶联目的的试验失败了。因此，我们在这里尝试了新的方法来合成携带一个或两个甘氨酸基团且带有自由羧基的杂环化合物，以便在一方面便于进一步的肽键合成，另一方面可以形成金属螯合物，这种性质对毒理学行为具有显著的影响。