2-[5-(1-Ethyl-3,3-dimethyl-5-sulfoindol-1-ium-2-yl)penta-2,4-dienylidene]-1-[6-[2-[2-[2-[[4-[[2-(4-methoxyphenyl)-1-oxo-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl]amino]-4-oxobutanoyl]amino]ethoxy]ethoxy]ethylamino]-6-oxohexyl]-3,3-dimethylindole-6-sulfonate | 1359959-44-6

• 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-[5-(1-Ethyl-3,3-dimethyl-5-sulfoindol-1-ium-2-yl)penta-2,4-dienylidene]-1-[6-[2-[2-[2-[[4-[[2-(4-methoxyphenyl)-1-oxo-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl]amino]-4-oxobutanoyl]amino]ethoxy]ethoxy]ethylamino]-6-oxohexyl]-3,3-dimethylindole-6-sulfonate
• 英文别名: 2-[5-(1-ethyl-3,3-dimethyl-5-sulfoindol-1-ium-2-yl)penta-2,4-dienylidene]-1-[6-[2-[2-[2-[[4-[[2-(4-methoxyphenyl)-1-oxo-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl]amino]-4-oxobutanoyl]amino]ethoxy]ethoxy]ethylamino]-6-oxohexyl]-3,3-dimethylindole-6-sulfonate
• CAS: 1359959-44-6
• 化学式: C₅₉H₆₉N₉O₁₃S₂
• 分子量: 1176.38
• InChiKey: HCXPCPSUEGMFJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  83
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  298
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-4,15-dioxo-3,8,11-trioxa-5,14-diazaoctadecan-18-oic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 2-[5-(1-Ethyl-3,3-dimethyl-5-sulfoindol-1-ium-2-yl)penta-2,4-dienylidene]-1-[6-[2-[2-[2-[[4-[[2-(4-methoxyphenyl)-1-oxo-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl]amino]-4-oxobutanoyl]amino]ethoxy]ethoxy]ethylamino]-6-oxohexyl]-3,3-dimethylindole-6-sulfonate
  参考文献：
  名称：

  Highly Potent and Selective Fluorescent Antagonists of the Human Adenosine A₃ Receptor Based on the 1,2,4-Triazolo[4,3-a]quinoxalin-1-one Scaffold

  摘要：

  The adenosine-A(3) receptor (A(3)AR) is a G protein-coupled receptor that shows promise as a therapeutic target for cancer, glaucoma, and various autoimmune inflammatory disorders, and as such, there is a need for molecular probes to study this receptor. Here, we report a series of fluorescent ligands containing different linkers and fluorophores based around a 1,2,4-triazolo[4,3-a]quinoxalin-1-one antagonist. One of these conjugates (19) displayed high affinity for the A(3)AR (pK(D) = 9.36 +/- 0.12) and is >650-fold selective over other adenosine receptor subtypes. Confocal microscopy revealed clear, displaceable membrane labeling of CHO-A(3) cells with 19, with no detectable labeling of CHO-A(1) cells under identical conditions. This fluorescent ligand was also able to specifically label the A(3)AR in HEK293T cells containing a mixed adenosine receptor population. The subtype specificity, along with its excellent imaging properties, make 19 an ideal tool for studying A(3)AR distribution and organization, particularly in the presence of other adenosine receptor subtypes.

  DOI：

  10.1021/jm201722y

文献信息

• Highly Potent and Selective Fluorescent Antagonists of the Human Adenosine A₃ Receptor Based on the 1,2,4-Triazolo[4,3-<i>a</i>]quinoxalin-1-one Scaffold
  作者：Andrea J. Vernall、Leigh A. Stoddart、Stephen J. Briddon、Stephen J. Hill、Barrie Kellam

  DOI：10.1021/jm201722y

  日期：2012.2.23

  The adenosine-A(3) receptor (A(3)AR) is a G protein-coupled receptor that shows promise as a therapeutic target for cancer, glaucoma, and various autoimmune inflammatory disorders, and as such, there is a need for molecular probes to study this receptor. Here, we report a series of fluorescent ligands containing different linkers and fluorophores based around a 1,2,4-triazolo[4,3-a]quinoxalin-1-one antagonist. One of these conjugates (19) displayed high affinity for the A(3)AR (pK(D) = 9.36 +/- 0.12) and is >650-fold selective over other adenosine receptor subtypes. Confocal microscopy revealed clear, displaceable membrane labeling of CHO-A(3) cells with 19, with no detectable labeling of CHO-A(1) cells under identical conditions. This fluorescent ligand was also able to specifically label the A(3)AR in HEK293T cells containing a mixed adenosine receptor population. The subtype specificity, along with its excellent imaging properties, make 19 an ideal tool for studying A(3)AR distribution and organization, particularly in the presence of other adenosine receptor subtypes.