2-(4-bromobenzyl)-4-(3-methoxybenzyl)-6-methyl-pyridazin-3(2H)-one | 1184304-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-bromobenzyl)-4-(3-methoxybenzyl)-6-methyl-pyridazin-3(2H)-one
• 英文别名: 2-[(4-Bromophenyl)methyl]-4-[(3-methoxyphenyl)methyl]-6-methylpyridazin-3-one
• CAS: 1184304-46-8
• 化学式: C₂₀H₁₉BrN₂O₂
• 分子量: 399.287
• InChiKey: SULJMMYTHOZFTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(3-methoxybenzyl)-6-methylpyridazin-3(2H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以68%的产率得到2-(4-bromobenzyl)-4-(3-methoxybenzyl)-6-methyl-pyridazin-3(2H)-one
  参考文献：
  名称：

  6-Methyl-2,4-Disubstituted Pyridazin-3(2H)-ones: A Novel Class of Small-Molecule Agonists for Formyl Peptide Receptors

  摘要：

  Following a ligand-based drug design approach, a potent mixed formyl peptide receptor I (FPR1) and formyl peptide receptor-like I (FPRL1) agonist (14a) and a potent and specific FPRL1 agonist (14x) were identified. These compounds belong to a large series of pyridazin-3(2H)-one derivatives substituted with methyl group at position 6 and a methoxy benzyl at position 4. At position 2, an acetamide side chain is essential for activity. Likewise, the presence of lipophilic and/or electronegative substituents in the position para to the aryl group at the end of the chain plays a critical role for activity. Affinity for FPR1 receptors was evaluated by measuring intracellular calcium flux in HL-60 cells transfected with FPR1, FPRL1, and FPRL2, Agonists were able to activate intracellular calcium mobilization and chemotaxis in human neutrophils. The most potent chemotactic agent (EC50 = 0.6 mu M) was the mixed FPR/FPRL1 agonist 14h.

  DOI：

  10.1021/jm900592h