(2S)-2-amino-4-(hydroxy(hydroxy(4-hydroxy-3-methoxy-5-nitrophenyl)methyl)phosphoryl)butanoic acid hydrochloride | 1525684-18-7

• 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: (2S)-2-amino-4-(hydroxy(hydroxy(4-hydroxy-3-methoxy-5-nitrophenyl)methyl)phosphoryl)butanoic acid hydrochloride
• 英文别名: LSP1-2111；[(1S)-1-carboxy-3-[hydroxy-[hydroxy-(4-hydroxy-3-methoxy-5-nitrophenyl)methyl]phosphoryl]propyl]azanium;chloride
• CAS: 1525684-18-7
• 化学式: C₁₂H₁₇N₂O₉P*ClH
• 分子量: 400.71
• InChiKey: DHENNBRLHNYRPJ-ADEFDSRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  196
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  ((S)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutyl)(hydroxy(4-hydroxy-3-methoxy-5-nitrophenyl)methyl)phosphinic acid 在 盐酸 作用下， 以 水 为溶剂， 以35.1%的产率得到(2S)-2-amino-4-(hydroxy(hydroxy(4-hydroxy-3-methoxy-5-nitrophenyl)methyl)phosphoryl)butanoic acid hydrochloride
  参考文献：
  名称：

  Qualification of LSP1-2111 as a Brain Penetrant Group III Metabotropic Glutamate Receptor Orthosteric Agonist

  摘要：

  LSP1-2111 is a group III metabotropic glutamate receptor agonist with preference toward the mGlu4 receptor subtype. This compound has been extensively used as a tool to explore the pharmacology of mGlu4 receptor activation in preclinical animal behavioral models. However, the blood-brain barrier penetration of this amino acid derivative has never been studied. We report studies on the central nervous system (CNS) disposition of LSP1-2111 using quantitative microdialysis in rat. Significant unbound concentrations of the drug relative to its in vitro binding affinity and functional potency were established in extracellular fluid (ECF). These findings support the use of LSP1-2111 to study the CNS pharmacology of mGlu4 receptor activation through orthosteric agonist mechanisms.

  DOI：

  10.1021/ml400338f

文献信息

• Qualification of LSP1-2111 as a Brain Penetrant Group III Metabotropic Glutamate Receptor Orthosteric Agonist
  作者：Manuel Cajina、Megan Nattini、Dekun Song、Gennady Smagin、Erling B. Jørgensen、Gamini Chandrasena、Christoffer Bundgaard、Dorthe Bach Toft、Xinyan Huang、Francine Acher、Dario Doller

  DOI：10.1021/ml400338f

  日期：2014.2.13

  LSP1-2111 is a group III metabotropic glutamate receptor agonist with preference toward the mGlu4 receptor subtype. This compound has been extensively used as a tool to explore the pharmacology of mGlu4 receptor activation in preclinical animal behavioral models. However, the blood-brain barrier penetration of this amino acid derivative has never been studied. We report studies on the central nervous system (CNS) disposition of LSP1-2111 using quantitative microdialysis in rat. Significant unbound concentrations of the drug relative to its in vitro binding affinity and functional potency were established in extracellular fluid (ECF). These findings support the use of LSP1-2111 to study the CNS pharmacology of mGlu4 receptor activation through orthosteric agonist mechanisms.