3-<(4-acetyl-3-fluorophenoxy)methyl>nitrobenzene | 98646-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<(4-acetyl-3-fluorophenoxy)methyl>nitrobenzene
• 英文别名: 3-[(4-acetyl-3-fluorophenoxy)methyl]nitrobenzene；1-[2-Fluoro-4-[(3-nitrophenyl)methoxy]phenyl]ethanone
• CAS: 98646-39-0
• 化学式: C₁₅H₁₂FNO₄
• 分子量: 289.263
• InChiKey: WQQQDQBJKYEAIG-UHFFFAOYSA-N

物化性质

• 沸点：
  451.6±35.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<(4-acetyl-3-fluorophenoxy)methyl>nitrobenzene 在 盐酸 、 铁粉 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 31.0h， 生成 1-[3-(4-Acetyl-3-fluoro-phenoxymethyl)-phenyl]-5-oxo-pyrrolidine-3-carboxylic 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：

  3-氟苯酚 在 三氯化铝 、 potassium carbonate 、 caesium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 111.5h， 生成 3-<(4-acetyl-3-fluorophenoxy)methyl>nitrobenzene
  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

• Aromatic compounds as antiallergic agents
  申请人：American Home Products Corporation

  公开号：US04528392A1

  公开（公告）日：1985-07-09

  There are disclosed compounds of the formula ##STR1## wherein X is OR.sup.2, SR.sup.2, N(R.sup.2).sub.2 or halo; W is --CH.sub.2 --, ##STR2## Y is --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 S--, --SCH.sub.2 --, ##STR3## m is 0-6; n is 0-6; p is 1-3; A is O or S; B is OR.sup.2, SR.sup.2 or N(R.sup.2).sub.2 ; R.sup.1 is hydrogen, loweralkyl, loweralkoxy or halo; R.sup.2 is hydrogen or loweralkyl; and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like.

  公开了以下式子的化合物：##STR1## 其中X为OR.sup.2，SR.sup.2，N（R.sup.2）.sub.2或卤素；W为--CH.sub.2 --，##STR2## Y为--CH.sub.2 O--，--OCH.sub.2 --，--CH.sub.2 S--，--SCH.sub.2 --，##STR3## m为0-6；n为0-6；p为1-3；A为O或S；B为OR.sup.2，SR.sup.2或N（R.sup.2）.sub.2；R.sup.1为氢，较低烷基，较低烷氧基或卤素；R.sup.2为氢或较低烷基；以及其药学上可接受的盐，并将其用于治疗白三烯介导的鼻-支气管阻塞性通气道疾病，如过敏性鼻炎、过敏性支气管哮喘等。
• US4528392A
  申请人：——

  公开号：US4528392A

  公开（公告）日：1985-07-09
• 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.