AG-3 | 1428637-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: AG-3
• CAS: 1428637-44-8
• 化学式: C₁₀H₁₁N₅*ClH
• 分子量: 237.692
• InChiKey: WHAKMQNJSIHCPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.05
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 肼甲酰亚胺酰胺一氯化氢 以 乙醇 为溶剂， 反应 5.0h， 生成 AG-3
  参考文献：
  名称：

  氨基胍Hy衍生物作为非肽NPFF1受体拮抗剂可逆阿片类药物引起的痛觉过敏。

  摘要：

  先前已显示神经肽FF受体（NPFF1R和NPFF2R）及其内源性配体神经肽FF具有抗阿片类药物的特性，并且在鸦片类药物长期服用相关的不良反应中起关键作用，包括阿片类药物引起的痛觉过敏和镇痛耐受性的发展。在这项工作中，我们试图通过将我们的注意力集中在一系列杂环上来鉴定新的NPFF受体配体，这些杂环作为刚性化的非肽NPFF受体配体，从已经描述的氨基胍（AGH）开始。结合实验和功能测定突出了用于体内实验的AGH 1n及其刚性化类似物2-氨基-二氢嘧啶22e。如先前使用原型二肽拮抗剂RF9所示，1n和22e均显着降低了芬太尼诱导的鼠持久性痛觉过敏。总而言之，这些数据表明，AGH硬化对两种NPFF受体均保持纳摩尔亲和力，同时改善了对NPFF1R的拮抗特性。

  DOI：

  10.1021/acschemneuro.8b00099

文献信息

• Improving the inhibitory activity of arylidenaminoguanidine compounds at the N-methyl-d-aspartate receptor complex from a recursive computational-experimental structure–activity relationship study
  作者：Joshua R. Ring、Fang Zheng、Aaron J. Haubner、John M. Littleton、Peter A. Crooks

  DOI：10.1016/j.bmc.2013.01.051

  日期：2013.4

  Using a combination of both the partial least squares (PLS) and back-propagation artificial neural network (ANN) pattern recognition methods, several models have been developed to predict the activity of a series of arylidenaminoguanidine analogs as inhibitory modulators of the N-methyl-D-aspartate receptor complex. This was done by correlating structural and physicochemical descriptors obtained from computation software with the experimentally observed [H-3]MK-801 displacement ability of a small library of synthesized and in vitro screened arylidenaminoguanidines. Results for the generated PLS model were r(2) = 0.814, rmsd = 0.208, r(CV)(2) = 0.714, loormsd = 0.261. The ANN model was created utilizing the eleven descriptors from the PLS model for comparison. The quality of the ANN model (r(2)=0.828, rmsd = 0.200, r(CV)(2) = 0.721, loormsd = 0.257) is similar to the PLS model, and indicates that the feature between the inputs and the output is majorly linear. These computational models were able to predict inhibition of the NMDA receptor complex by this series of compounds in silico, affording a predictive structure-based 'pre-screening' paradigm for the arylideneaminoguanidine analogs. (C) 2013 Elsevier Ltd. All rights reserved.
• Aminoguanidine Hydrazone Derivatives as Nonpeptide NPFF1 Receptor Antagonists Reverse Opioid Induced Hyperalgesia
  作者：Hassan Hammoud、Khadija Elhabazi、Raphäelle Quillet、Isabelle Bertin、Valérie Utard、Emilie Laboureyras、Jean-Jacques Bourguignon、Frédéric Bihel、Guy Simonnet、Frédéric Simonin、Martine Schmitt

  DOI：10.1021/acschemneuro.8b00099

  日期：2018.11.21

  this work, we sought to identify novel NPFF receptors ligands by focusing our interest in a series of heterocycles as rigidified nonpeptide NPFF receptor ligands, starting from already described aminoguanidine hydrazones (AGHs). Binding experiments and functional assays highlighted AGH 1n and its rigidified analogue 2-amino-dihydropyrimidine 22e for in vivo experiments. As shown earlier with the prototypical

  先前已显示神经肽FF受体（NPFF1R和NPFF2R）及其内源性配体神经肽FF具有抗阿片类药物的特性，并且在鸦片类药物长期服用相关的不良反应中起关键作用，包括阿片类药物引起的痛觉过敏和镇痛耐受性的发展。在这项工作中，我们试图通过将我们的注意力集中在一系列杂环上来鉴定新的NPFF受体配体，这些杂环作为刚性化的非肽NPFF受体配体，从已经描述的氨基胍（AGH）开始。结合实验和功能测定突出了用于体内实验的AGH 1n及其刚性化类似物2-氨基-二氢嘧啶22e。如先前使用原型二肽拮抗剂RF9所示，1n和22e均显着降低了芬太尼诱导的鼠持久性痛觉过敏。总而言之，这些数据表明，AGH硬化对两种NPFF受体均保持纳摩尔亲和力，同时改善了对NPFF1R的拮抗特性。