((S)-4-(6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanamido)cyclopent-1-en-1-yl)(butyl)phosphinic acid | 1425330-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: ((S)-4-(6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanamido)cyclopent-1-en-1-yl)(butyl)phosphinic acid
• 英文别名: butyl-[(4S)-4-[6-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanoylamino]cyclopenten-1-yl]phosphinic acid
• CAS: 1425330-37-5
• 化学式: C₂₁H₃₀N₅O₆P
• 分子量: 479.473
• InChiKey: GDIVWRNNXLWAKH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 4-二甲氨基吡啶 、 碳酸氢钠 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 ((S)-4-(6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanamido)cyclopent-1-en-1-yl)(butyl)phosphinic acid
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Fluorescent and Biotinylated Antagonists of ρ₁ GABA_C Receptors

  摘要：

  The rho(1) GABA(C) receptor is a ligand-gated chloride ion channel that shows promise as a therapeutic target for myopia, sleep disorders, memory and learning facilitation, and anxiety-related disorders. As such, there is a need for molecular probes to understand the role GABA(C) receptors play in physiological and pathological processes. To date, no labeled (either radioactive or fluorescent) GABA(C) selective ligand has been developed that can act as a marker for GABA(C) receptor visualization and localization studies. Herein, we report a series of fluorescent ligands containing different-sized linkers and fluorophores based around (S)-4-ACPBPA [(4-aminocyclopenten-1-yl)-butylphosphinic acid], a selective GABA(C) antagonist. One of these conjugates, (S)-4-ACPBPA-C5-BODIPY (13), displayed moderate potency (IC50 = 58.61 mu M) and selectivity (>100 times) for rho(1) over alpha(1)beta(2)gamma(2L) GABA(A) receptors. These conjugates are novel lead agents for the development of more potent and selective fluorescent probes for studying the localization and function of GABA(C) receptors in living cells.

  DOI：

  10.1021/ml300476v