3,6-dichloro-2-(4-methylpiperazin-1-yl)quinoxaline | 848837-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3,6-dichloro-2-(4-methylpiperazin-1-yl)quinoxaline
• 英文别名: 3,6-Dichloro-2-(4-methyl-piperazin-1-yl)-quinoxaline
• CAS: 848837-28-5
• 化学式: C₁₃H₁₄Cl₂N₄
• 分子量: 297.187
• InChiKey: QBVSIPOVHUBWTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dichloro-2-(4-methylpiperazin-1-yl)quinoxaline 、 2,6-dichloro-3-(4-methyl-piperazin-1-yl)-quinoxaline 在 lithium hydroxide 作用下， 反应 16.0h， 生成 6-chloro-3-(4-methyl-piperazin-1-yl)-1H-quinoxalin-2-one 、 7-chloro-3-(4-methylpiperazin-1-yl)quinoxalin-2(1H)-one
  参考文献：
  名称：

  Quinoxaline compounds

  摘要：

  喹诺醌化合物、组合物、制备方法，以及在白细胞召集抑制、调节H4受体以及治疗炎症、H4受体介导的疾病和相关疾病中使用它们的方法。

  公开号：

  US20050070527A1
• 作为产物：
  描述：

  7-chloro-3-(4-methylpiperazin-1-yl)quinoxalin-2(1H)-one 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以84%的产率得到3,6-dichloro-2-(4-methylpiperazin-1-yl)quinoxaline
  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

文献信息

• QUINOXALINE COMPOUNDS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1670774A1

  公开（公告）日：2006-06-21
• [EN] QUINOXALINE COMPOUNDS<br/>[FR] COMPOSES DE QUINOXALINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005033088A1

  公开（公告）日：2005-04-14

  Quinoxaline compounds, compositions, methods of making them, and methods of using them in leukocyte recruitment inhibition, in modulating an H4 receptor, and in treating conditions such as inflammation, H4 receptor-mediated conditions, and related conditions. Formula (I): wherein B is, independently from other member and substituent assignments, N or CR7; Y is independently from other member and substituent assignments, O, S or NH; n is, independently from member and substituent assignments, 1 or 2.
• Quinoxaline compounds
  申请人：Edwards P. James

  公开号：US20050070527A1

  公开（公告）日：2005-03-31

  Quinoxaline compounds, compositions, methods of making them, and methods of using them in leukocyte recruitment inhibition, in modulating an H 4 receptor, and in treating conditions such as inflammation, H 4 receptor-mediated conditions, and related conditions.

  喹诺醌化合物、组合物、制备方法，以及在白细胞召集抑制、调节H4受体以及治疗炎症、H4受体介导的疾病和相关疾病中使用它们的方法。
• Structure-Activity Relationships of Quinoxaline-Based 5-HT₃A and 5-HT₃AB Receptor-Selective Ligands
  作者：Andrew J. Thompson、Mark H. P. Verheij、Jacqueline E. van Muijlwijk-Koezen、Sarah C. R. Lummis、Rob Leurs、Iwan J. P. de Esch

  DOI：10.1002/cmdc.201300032

  日期：2013.6

  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.