N¹-(1-(4-([1,1′-biphenyl]-2-ylcarboxamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N4-((1-(20-amino-3,6,9,12,15,18-hexaoxaicosyl)-1H-1,2,3-triazol-4-yl)methyl)succinamide | 1384054-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-(1-(4-([1,1′-biphenyl]-2-ylcarboxamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N4-((1-(20-amino-3,6,9,12,15,18-hexaoxaicosyl)-1H-1,2,3-triazol-4-yl)methyl)succinamide
• 英文别名: N-[[1-[2-[2-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]triazol-4-yl]methyl]-N'-[1-[4-[(2-phenylbenzoyl)amino]benzoyl]-2,3,4,5-tetrahydro-1-benzazepin-5-yl]butanediamide
• CAS: 1384054-50-5
• 化学式: C₅₁H₆₄N₈O₁₀
• 分子量: 949.117
• InChiKey: PLBVORDZYASNOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  69
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  220
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N¹-(1-(4-([1,1′-biphenyl]-2-ylcarboxamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N4-((1-(20-amino-3,6,9,12,15,18-hexaoxaicosyl)-1H-1,2,3-triazol-4-yl)methyl)succinamide 、 DY647-N-hydroxysuccinimidyl ester 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  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：

  二氢-3-(异十二碳烯基)呋喃-2,5-二酮 在 盐酸 、 氯化亚砜 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 ammonium acetate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、100.0 kPa 条件下， 反应 34.75h， 生成 N¹-(1-(4-([1,1′-biphenyl]-2-ylcarboxamido)benzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-N4-((1-(20-amino-3,6,9,12,15,18-hexaoxaicosyl)-1H-1,2,3-triazol-4-yl)methyl)succinamide
  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