3-[[3-[(4-acetyl-3-fluorophenoxy)methyl]phenyl]amino]-3-oxopropanoic acid, methyl ester | 98619-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[[3-[(4-acetyl-3-fluorophenoxy)methyl]phenyl]amino]-3-oxopropanoic acid, methyl ester
• 英文别名: N-[3-(4-Acetyl-3-fluoro-phenoxymethyl)-phenyl]-malonamic acid methyl ester；methyl 3-[3-[(4-acetyl-3-fluorophenoxy)methyl]anilino]-3-oxopropanoate
• CAS: 98619-12-6
• 化学式: C₁₉H₁₈FNO₅
• 分子量: 359.354
• InChiKey: XLOYPGFCGATBTE-UHFFFAOYSA-N

物化性质

• 沸点：
  564.7±50.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氟苯酚 在 盐酸 、 三氯化铝 、 铁粉 、 potassium carbonate 、 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 128.5h， 生成 3-[[3-[(4-acetyl-3-fluorophenoxy)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

文献信息

• Synthesis and antiallergic activity of a novel series of 5-lipoxygenase inhibitors
  作者：Kenneth L. Kees、John H. Musser、Joseph Chang、Maureen Skowronek、Alan J. Lewis

  DOI：10.1021/jm00161a031

  日期：1986.11

  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.