4-amino-2-(3-methoxybenzyl)-6-methylpyridazin-3(2H)-one | 1184304-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-amino-2-(3-methoxybenzyl)-6-methylpyridazin-3(2H)-one
• 英文别名: 4-Amino-2-[(3-methoxyphenyl)methyl]-6-methylpyridazin-3-one
• CAS: 1184304-34-4
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: XRCYXPKGBSXJQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-2-(3-methoxybenzyl)-6-methylpyridazin-3(2H)-one 、 4-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以28%的产率得到4-bromo-N-[2-(3-methoxybenzyl)-6-methyl-3-oxo-2,3-dihydropyridazin-4-yl]benzamide
  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
• 作为产物：
  描述：

  2-(3-methoxybenzyl)-6-methylpyridazin-3(2H)-one 在 一水合肼 作用下， 反应 12.0h， 生成 4-amino-2-(3-methoxybenzyl)-6-methylpyridazin-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