4-chloro-5-methoxy-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one | 898261-84-2

• 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: 4-chloro-5-methoxy-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one
• 英文别名: 4-chloro-5-methoxy-2-(β-N-morpholinoethyl)-3(2H)-pyridazinone；4-chloro-5-methoxy-2-(2-morpholin-4-ylethyl)pyridazin-3-one
• CAS: 898261-84-2
• 化学式: C₁₁H₁₆ClN₃O₃
• 分子量: 273.719
• InChiKey: CSWBPSCPLPXLFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-5-methoxy-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one 、 (S)-2-(2,6-dichloro-benzoylamino)-3-(4-boronophenyl)-propionic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以42%的产率得到(2S)-2-[(2,6-dichlorophenyl)formamido]-3-(4-{5-methoxy-2-[2-(morpholin-4-yl)ethyl]-3-oxo-2,3-dihydropyridazin-4-yl}phenyl)propanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Pyridazinone-Based α₄ Integrin Receptor Antagonists

  摘要：

  A novel series of pyridazinone-functionalized phenylalanine analogues was prepared and evaluated for inhibition of cellular adhesion mediated by alpha(4)beta(1)/VCAM-1 and alpha(4)beta(7)/MAdCAM-1 interactions. Concise syntheses were developed and applied for exploration of structure-activity relationships pertaining to the pyridazinone ring as well as the N-acyl phenylalanine scaffold. Potent dual antagonists of alpha(4)beta(1) and alpha(4)beta(7) were generated from an amide subseries; antagonists selective for alpha(4)beta(7) were identified from urea and carbamate-based subseries. The pharmacokinetic properties of selected members of the series have been determined in rats and demonstrate that the use of ester prodrugs and alterations to the amide linkage can lead to improved oral bioavailability in this series. An alpha(4),beta(7)-selective member of the carbamate subseries (36c), upon oral admininstration, demonstrated in vivo efficacy in the mouse DSS colitis model.

  DOI：

  10.1021/jm060031q
• 作为产物：
  描述：

  4-(2-氯乙基)吗啉 、 4-氯-5-甲氧基哒嗪-3(2H)-酮 在 potassium carbonate 作用下， 生成 4-chloro-5-methoxy-2-(2-morpholin-4-yl-ethyl)-2H-pyridazin-3-one
  参考文献：
  名称：

  4-氯-5-甲氧基-3(2H)-哒嗪酮与三氟乙基化试剂反应过程中甲基碳正离子的迁移

  摘要：

  4-氯-5-甲氧基-2-(β-三氟乙基)-3(2H)-哒嗪酮(4)，4-氯-5-甲氧基-3(2H)-哒嗪酮(5)与RCH2CF3反应合成4-氯-5-甲氧基-2-(β-三氟乙基)-3(2H)-哒嗪酮(4)研究了不同溶剂中的 (R = I, TsO, MsO, TfO)。发现在该反应过程中发生了甲基迁移。氧鎓盐 9 被认为是形成副产物 4-chloro-5-methoxy-2-methyl-3(2H)-pyridazinone (7) 和 4-chloro-2-methyl-5-(β) 的活性中间体-三氟乙氧基)-3(2)-哒嗪酮(8)。

  DOI：

  10.3390/molecules14020777