5-(N-(4-carboxybutyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl) benzenesulfonate | 1384054-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-(N-(4-carboxybutyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl) benzenesulfonate
• 英文别名: 5-(4-Carboxybutylsulfamoyl)-2-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzenesulfonate；5-(4-carboxybutylsulfamoyl)-2-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]benzenesulfonate
• CAS: 1384054-45-8
• 化学式: C₃₂H₃₉N₃O₈S₂
• 分子量: 657.809
• InChiKey: YNCWRFOEDWPCJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(4-(5-amino-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)phenyl)-[1,1′-biphenyl]-2-carboxamide 、 5-(N-(4-carboxybutyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl) benzenesulfonate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 以67%的产率得到5-((4-(3-((1-(4-([1,1′-biphenyl]-2-ylcarboxamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amino)-3-oxopropyl)piperazin-1-yl)sulfonyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl)benzenesulfonate
  参考文献：
  名称：

  Selective Fluorescent Nonpeptidic Antagonists For Vasopressin V₂ GPCR: Application To Ligand Screening and Oligomerization Assays.

  摘要：

  A series of fluorescent benzazepine ligands for the arginine-vasopressin V-2 receptor (AVP V2R) was synthesized using "Click" chemistry. Their in vitro pharmacological profile at AVP V2R, V1aR, V1bR, and oxytocin receptor was measured by binding assay and functional studies. Compound 9p, labeled with Lissamine Rhodamine B using novel solid-phase organic tagging (SPOrT) resin, exhibited a high affinity for V2R (4.0 nM), an excellent selectivity toward V2R and antagonist properties. By changing the nature of the dye, DY647 and Lumi4-Tb probes 44 and 47 still display a high affinity for V2R (5.6 and 5.8 nM, respectively). These antagonists constitute the first high-affinity selective nonpeptidic fluorescent ligands for V2R. They enabled the development of V2R time-resolved FRET-based assay readily amenable to high-throughput screening. Taking advantage of their selectivity, these compounds were also successfully involved in the study of V1aR-V2R dimerization on cell surface.

  DOI：

  10.1021/jm3006146
• 作为产物：
  描述：

  C₂₉H₃₄N₂O₇S₂*Na⁽¹⁺⁾ 在 4-二甲氨基吡啶 、 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 5-(N-(4-carboxybutyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl) benzenesulfonate
  参考文献：
  名称：

  Selective Fluorescent Nonpeptidic Antagonists For Vasopressin V₂ GPCR: Application To Ligand Screening and Oligomerization Assays.

  摘要：

  A series of fluorescent benzazepine ligands for the arginine-vasopressin V-2 receptor (AVP V2R) was synthesized using "Click" chemistry. Their in vitro pharmacological profile at AVP V2R, V1aR, V1bR, and oxytocin receptor was measured by binding assay and functional studies. Compound 9p, labeled with Lissamine Rhodamine B using novel solid-phase organic tagging (SPOrT) resin, exhibited a high affinity for V2R (4.0 nM), an excellent selectivity toward V2R and antagonist properties. By changing the nature of the dye, DY647 and Lumi4-Tb probes 44 and 47 still display a high affinity for V2R (5.6 and 5.8 nM, respectively). These antagonists constitute the first high-affinity selective nonpeptidic fluorescent ligands for V2R. They enabled the development of V2R time-resolved FRET-based assay readily amenable to high-throughput screening. Taking advantage of their selectivity, these compounds were also successfully involved in the study of V1aR-V2R dimerization on cell surface.

  DOI：

  10.1021/jm3006146

文献信息

• Selective Fluorescent Nonpeptidic Antagonists For Vasopressin V₂ GPCR: Application To Ligand Screening and Oligomerization Assays.
  作者：Stéphanie Loison、Martin Cottet、Hélène Orcel、Hélène Adihou、Rita Rahmeh、Laurent Lamarque、Eric Trinquet、Esther Kellenberger、Marcel Hibert、Thierry Durroux、Bernard Mouillac、Dominique Bonnet

  DOI：10.1021/jm3006146

  日期：2012.10.25

  A series of fluorescent benzazepine ligands for the arginine-vasopressin V-2 receptor (AVP V2R) was synthesized using "Click" chemistry. Their in vitro pharmacological profile at AVP V2R, V1aR, V1bR, and oxytocin receptor was measured by binding assay and functional studies. Compound 9p, labeled with Lissamine Rhodamine B using novel solid-phase organic tagging (SPOrT) resin, exhibited a high affinity for V2R (4.0 nM), an excellent selectivity toward V2R and antagonist properties. By changing the nature of the dye, DY647 and Lumi4-Tb probes 44 and 47 still display a high affinity for V2R (5.6 and 5.8 nM, respectively). These antagonists constitute the first high-affinity selective nonpeptidic fluorescent ligands for V2R. They enabled the development of V2R time-resolved FRET-based assay readily amenable to high-throughput screening. Taking advantage of their selectivity, these compounds were also successfully involved in the study of V1aR-V2R dimerization on cell surface.