tert-butyl (1-(3-chloroquinoxalin-2-yl)pyrrolidin-3-yl)(methyl)carbamate | 1500110-46-2

• 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: tert-butyl (1-(3-chloroquinoxalin-2-yl)pyrrolidin-3-yl)(methyl)carbamate
• 英文别名: tert-butyl N-[1-(3-chloroquinoxalin-2-yl)pyrrolidin-3-yl]-N-methylcarbamate
• CAS: 1500110-46-2
• 化学式: C₁₈H₂₃ClN₄O₂
• 分子量: 362.859
• InChiKey: ZBWOLXWXTGPABZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1-(3-chloroquinoxalin-2-yl)pyrrolidin-3-yl)(methyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以61%的产率得到1-(3-chloroquinoxalin-2-yl)-N-methylpyrrolidin-3-amine
  参考文献：
  名称：

  Structure-Activity Relationships of Quinoxaline-Based 5-HT₃A and 5-HT₃AB Receptor-Selective Ligands

  摘要：

  AbstractUntil recently, discriminating between homomeric 5‐HT3A and heteromeric 5‐HT3AB receptors was only possible with ligands that bind in the receptor pore. This study describes the first series of ligands that can discriminate between these receptor types at the level of the orthosteric binding site. During a recent fragment screen, 2‐chloro‐3‐(4‐methylpiperazin‐1‐yl)quinoxaline (VUF10166) was identified as a ligand that displays an 83‐fold difference in [3H]granisetron binding affinity between 5‐HT3A and 5‐HT3AB receptors. Fragment hit exploration, initiated from VUF10166 and 3‐(4‐methylpiperazin‐1‐yl)quinoxalin‐2‐ol, resulted in a series of compounds with higher affinity at either 5‐HT3A or 5‐HT3AB receptors. These ligands reveal that a single atom is sufficient to change the selectivity profile of a compound. At the extremes of the new compounds were 2‐amino‐3‐(4‐methylpiperazin‐1‐yl)quinoxaline, which showed 11‐fold selectivity for the 5‐HT3A receptor, and 2‐(4‐methylpiperazin‐1‐yl)quinoxaline, which showed an 8.3‐fold selectivity for the 5‐HT3AB receptor. These compounds represent novel molecular tools for studying 5‐HT3 receptor subtypes and could help elucidate their physiological roles.

  DOI：

  10.1002/cmdc.201300032
• 作为产物：
  描述：

  2,3-二氯喹喔啉 、 3-N-Boc-N-甲基氨基吡咯烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以0.68 g的产率得到tert-butyl (1-(3-chloroquinoxalin-2-yl)pyrrolidin-3-yl)(methyl)carbamate
  参考文献：
  名称：

  Structure-Activity Relationships of Quinoxaline-Based 5-HT₃A and 5-HT₃AB Receptor-Selective Ligands

  摘要：

  AbstractUntil recently, discriminating between homomeric 5‐HT3A and heteromeric 5‐HT3AB receptors was only possible with ligands that bind in the receptor pore. This study describes the first series of ligands that can discriminate between these receptor types at the level of the orthosteric binding site. During a recent fragment screen, 2‐chloro‐3‐(4‐methylpiperazin‐1‐yl)quinoxaline (VUF10166) was identified as a ligand that displays an 83‐fold difference in [3H]granisetron binding affinity between 5‐HT3A and 5‐HT3AB receptors. Fragment hit exploration, initiated from VUF10166 and 3‐(4‐methylpiperazin‐1‐yl)quinoxalin‐2‐ol, resulted in a series of compounds with higher affinity at either 5‐HT3A or 5‐HT3AB receptors. These ligands reveal that a single atom is sufficient to change the selectivity profile of a compound. At the extremes of the new compounds were 2‐amino‐3‐(4‐methylpiperazin‐1‐yl)quinoxaline, which showed 11‐fold selectivity for the 5‐HT3A receptor, and 2‐(4‐methylpiperazin‐1‐yl)quinoxaline, which showed an 8.3‐fold selectivity for the 5‐HT3AB receptor. These compounds represent novel molecular tools for studying 5‐HT3 receptor subtypes and could help elucidate their physiological roles.

  DOI：

  10.1002/cmdc.201300032