1-[4-(2-氨基-苄氧基)-2-羟基-苯基]-乙酮 | 103981-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-(2-氨基-苄氧基)-2-羟基-苯基]-乙酮
• 英文名称: 1-[4-[(2-Aminophenyl)methoxy]-2-hydroxyphenyl]ethanone
• 英文别名: 1-[4-[(2-aminophenyl)methoxy]-2-hydroxyphenyl]ethanone
• CAS: 103981-31-3
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: CRIMVDRZCVTETQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-(2-氨基-苄氧基)-2-羟基-苯基]-乙酮 、 丙二酸二甲酯 反应 2.0h， 以46%的产率得到3[[-[(4-acetyl-3-hydroxyphenoxy)methyl]phenyl]amino]-3-oxopropanoic acid, methyl ester
  参考文献：
  名称：

  Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors

  摘要：

  A series of novel substituted [[(phenoxymethyl)phenyl]amino]oxoalkanoic acid esters have been synthesized. These compounds were tested in vitro for their ability to inhibit the synthesis of 5-hydroxyeicosatetraenoic acid and leukotriene (LT) B4 from rat polymorphonuclear leukocytes (PMN) and in vivo as inhibitors ovalbumin- (OA) and LTD4-induced bronchospasm in the guinea pig. Compounds 5-12 and 25 had IC50's between 1 and 5.6 microM in the rat PMN 5-lipoxygenase assay. Compounds 1, 3, and 16 inhibited OA-induced bronchoconstriction (61%, 64%, and 57%, respectively), but only 1 showed activity against LTD4-induced bronchoconstriction. When tested against LTD4-induced contraction of isolated guinea pig tracheal spiral strips, 1 was a competitive inhibitor with a pKB of 4.94.

  DOI：

  10.1021/jm00161a031
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 盐酸 、 铁粉 、 potassium carbonate 、 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 15.5h， 生成 1-[4-(2-氨基-苄氧基)-2-羟基-苯基]-乙酮
  参考文献：
  名称：

  Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors

  摘要：

  A series of novel substituted [[(phenoxymethyl)phenyl]amino]oxoalkanoic acid esters have been synthesized. These compounds were tested in vitro for their ability to inhibit the synthesis of 5-hydroxyeicosatetraenoic acid and leukotriene (LT) B4 from rat polymorphonuclear leukocytes (PMN) and in vivo as inhibitors ovalbumin- (OA) and LTD4-induced bronchospasm in the guinea pig. Compounds 5-12 and 25 had IC50's between 1 and 5.6 microM in the rat PMN 5-lipoxygenase assay. Compounds 1, 3, and 16 inhibited OA-induced bronchoconstriction (61%, 64%, and 57%, respectively), but only 1 showed activity against LTD4-induced bronchoconstriction. When tested against LTD4-induced contraction of isolated guinea pig tracheal spiral strips, 1 was a competitive inhibitor with a pKB of 4.94.

  DOI：

  10.1021/jm00161a031