6-[4-(2-hydroxy-ethyl)-phenyl]-2H-pyridazin-3-one | 330200-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-[4-(2-hydroxy-ethyl)-phenyl]-2H-pyridazin-3-one
• 英文别名: 3-[4-(2-hydroxyethyl)phenyl]-1H-pyridazin-6-one
• CAS: 330200-37-8
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: RCCIJAVYRVPZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[4-(2-hydroxy-ethyl)-phenyl]-2H-pyridazin-3-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 6-{4-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-phenyl}-2H-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and evaluation of pyridazinone–phenethylamine derivatives as selective and orally bioavailable histamine H3 receptor antagonists with robust wake-promoting activity

  摘要：

  A series of pyridazinone-phenethylamine derivatives with moderate to low nanomolar affinity for rat and human H3R are described. These analogs exhibited excellent selectivity and metabolic stability, with acceptable rat pharmacokinetic properties. In vivo, 7 and 11 demonstrated potent H3R functional antagonism in the rat dipsogenia model and robust wake-promoting activity in the rat electroencephalogram/electromyography (EEG/EMG) model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.104
• 作为产物：
  描述：

  乙酸苯乙酯 在 aluminum (III) chloride 、 水 、 potassium carbonate 、 肼 作用下， 以 甲醇 、 1,2-二氯乙烷 、 异丙醇 为溶剂， 反应 11.5h， 生成 6-[4-(2-hydroxy-ethyl)-phenyl]-2H-pyridazin-3-one
  参考文献：
  名称：

  Synthesis and evaluation of pyridazinone–phenethylamine derivatives as selective and orally bioavailable histamine H3 receptor antagonists with robust wake-promoting activity

  摘要：

  A series of pyridazinone-phenethylamine derivatives with moderate to low nanomolar affinity for rat and human H3R are described. These analogs exhibited excellent selectivity and metabolic stability, with acceptable rat pharmacokinetic properties. In vivo, 7 and 11 demonstrated potent H3R functional antagonism in the rat dipsogenia model and robust wake-promoting activity in the rat electroencephalogram/electromyography (EEG/EMG) model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.104

文献信息

• Substituted Pyridazinone Derivatives as Histamine-3 (H3) Receptor Ligands
  申请人：Becknell Nadine C.

  公开号：US20110098269A1

  公开（公告）日：2011-04-28

  The present invention provides compounds according to Formulas I, II, III, IV, V, VI, VII or VIII: their use as H 3 antagonists/inverse agonists, processes for their preparation, and pharmaceutical compositions thereof.

  本发明提供了公式I、II、III、IV、V、VI、VII或VIII的化合物：它们作为H3拮抗剂/逆激动剂的用途、它们的制备方法以及它们的药物组成物。
• [EN] SUBSTITUTED PYRIDAZINONE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS PYRIDAZINONE SUBSTITUÉS COMME LIGANDS DES RÉCEPTEURS DE L'HISTAMINE-3 (H3)
  申请人：CEPHALON INC

  公开号：WO2009142732A3

  公开（公告）日：2010-10-28
• SUBSTITUTED PYRIDAZINONE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS
  申请人：Cephalon, Inc.

  公开号：EP2328586A2

  公开（公告）日：2011-06-08
• Synthesis and evaluation of pyridazinone–phenethylamine derivatives as selective and orally bioavailable histamine H3 receptor antagonists with robust wake-promoting activity
  作者：Reddeppa reddy Dandu、John A. Gruner、Joanne R. Mathiasen、Lisa D. Aimone、Greg Hostetler、Caitlyn Benfield、Robert J. Bendesky、Val R. Marcy、Rita Raddatz、Robert L. Hudkins

  DOI：10.1016/j.bmcl.2011.08.104

  日期：2011.11

  A series of pyridazinone-phenethylamine derivatives with moderate to low nanomolar affinity for rat and human H3R are described. These analogs exhibited excellent selectivity and metabolic stability, with acceptable rat pharmacokinetic properties. In vivo, 7 and 11 demonstrated potent H3R functional antagonism in the rat dipsogenia model and robust wake-promoting activity in the rat electroencephalogram/electromyography (EEG/EMG) model. (C) 2011 Elsevier Ltd. All rights reserved.