(S)-{2-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester | 1159633-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-{2-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 1159633-20-1
• 化学式: C₂₃H₂₈FN₅O₄
• 分子量: 457.505
• InChiKey: CSKRKZZBFWUTCX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-{2-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 24.5h， 以86%的产率得到(S)-2-amino-1-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-3-hydroxypropan-1-one hydrochloride
  参考文献：
  名称：

  Specific Targeting of Peripheral Serotonin 5-HT₃ Receptors. Synthesis, Biological Investigation, and Structure−Activity Relationships

  摘要：

  The synthesis and the biological characterization of novel highly selective pyrroloquinoxaline 5-HT3 receptor (5-HT3R) ligands are described. In functional and in vivo biological studies the novel quinoxalines modulated cardiac parameters by direct interaction with myocardial 5-HT(3)Rs. The potent 5-HT3R ligands 4h and 4n modulate chronotropy (right atrium) but not inotropy (left atrium) at the cardiac level, being antagonist and partial agonist, respectively. Preliminary pharmacokinetic studies indicate that (S)-4n and 4a, representatives of the novel 5-HT3R ligands, possess poor blood-brain barrier permeability, being the prototypes of peripherally acting 5-HT3R modulators endowed with a clear-cut pharmacological activity at the cardiac level. The unique properties of 4h and 4n, compared to their previously described centrally active N-methyl analogue 5a, are mainly due to the hydrophilic groups at the distal piperazine nitrogen. These analogues represent novel pharmacological tools for investigating the role of peripheral 5-HT3R in the modulation of cardiac parameters.

  DOI：

  10.1021/jm900018b
• 作为产物：
  描述：

  BOC-L-丝氨酸 、 7-Fluoro-4-piperazin-1-yl-pyrrolo[1,2-a]quinoxaline 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到(S)-{2-[4-(7-fluoropyrrolo[1,2-a]quinoxalin-4-yl)piperazin-1-yl]-1-hydroxymethyl-2-oxoethyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Specific Targeting of Peripheral Serotonin 5-HT₃ Receptors. Synthesis, Biological Investigation, and Structure−Activity Relationships

  摘要：

  The synthesis and the biological characterization of novel highly selective pyrroloquinoxaline 5-HT3 receptor (5-HT3R) ligands are described. In functional and in vivo biological studies the novel quinoxalines modulated cardiac parameters by direct interaction with myocardial 5-HT(3)Rs. The potent 5-HT3R ligands 4h and 4n modulate chronotropy (right atrium) but not inotropy (left atrium) at the cardiac level, being antagonist and partial agonist, respectively. Preliminary pharmacokinetic studies indicate that (S)-4n and 4a, representatives of the novel 5-HT3R ligands, possess poor blood-brain barrier permeability, being the prototypes of peripherally acting 5-HT3R modulators endowed with a clear-cut pharmacological activity at the cardiac level. The unique properties of 4h and 4n, compared to their previously described centrally active N-methyl analogue 5a, are mainly due to the hydrophilic groups at the distal piperazine nitrogen. These analogues represent novel pharmacological tools for investigating the role of peripheral 5-HT3R in the modulation of cardiac parameters.

  DOI：

  10.1021/jm900018b