1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one | 103981-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one
• CAS: 103981-23-3
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: BUSWJKWSHMZPMS-UHFFFAOYSA-N

物化性质

• 沸点：
  515.5±40.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one 、 丁二酸单甲酯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以37%的产率得到4-[[3-[[3-hydroxy-4-(1-oxohexyl)phenoxy]methyl]phenyl]amino]-4-oxobutanoic 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：

  1-[2-Hydroxy-4-[(3-nitrophenyl)methoxy]phenyl]-1-hexanone 在 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one
  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