(2S,3E)-4-溴-1-(4-氟苯氧基)-3-丁烯-2-醇 | 524714-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2S,3E)-4-溴-1-(4-氟苯氧基)-3-丁烯-2-醇
• 英文名称: (1E,3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butene
• 英文别名: (2S,3E)-4-Bromo-1-(4-fluorophenoxy)-3-buten-2-ol；(E,2S)-4-bromo-1-(4-fluorophenoxy)but-3-en-2-ol
• CAS: 524714-06-5
• 化学式: C₁₀H₁₀BrFO₂
• 分子量: 261.091
• InChiKey: BCBQENYDWQAHMZ-CYNONHLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3E)-4-溴-1-(4-氟苯氧基)-3-丁烯-2-醇 在 盐酸 、 正丙胺 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.03h， 生成 methyl (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxyhexadeca-7,9,13-trien-11-ynoate
  参考文献：
  名称：

  Synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, an analogue of 15R-Lipoxin A4

  摘要：

  We describe a method for the synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, a compound that has been described as a metabolically stable analogue of 15R-lipoxin A(4). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00667-x
• 作为产物：
  描述：

  1-(4-氟苯氧基)丁-3-炔-2-醇 在 偶氮二异丁腈 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3E)-4-溴-1-(4-氟苯氧基)-3-丁烯-2-醇
  参考文献：
  名称：

  Synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, an analogue of 15R-Lipoxin A4

  摘要：

  We describe a method for the synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, a compound that has been described as a metabolically stable analogue of 15R-lipoxin A(4). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00667-x

文献信息

• Lipoxin A4 analogs
  申请人：Schering Aktiengesellschaft

  公开号：US20040162433A1

  公开（公告）日：2004-08-19

  This invention is directed to lipoxin A 4 analogs of the following formula (I) and (II): 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are described herein. These analogs are useful in treating inflammatory and autoimmune disorders in humans. These analogs are also useful in treating pulmonary or respiratory tract inflammation in humans.

  本发明涉及以下公式（I）和（II）的脂氧素A4类似物：1其中R1，R2，R3，R4和R5如本文所述。这些类似物在治疗人类的炎症和自身免疫性疾病方面非常有用。这些类似物还在治疗人类的肺部或呼吸道炎症方面非常有用。
• Intermediates for the preparation of lipoxin A4 analogs
  申请人：Grossbach Danja

  公开号：US20070105949A1

  公开（公告）日：2007-05-10

  This invention is directed to compounds useful as intermediates in the synthesis of lipoxin A 4 analogs of the following formulas (I) and (II): wherein R 1 , R 2 , R 3 , R 4 and R 5 are described herein. These analogs are useful in treating inflammatory and autoimmune disorders in humans. These analogs are also useful in treating pulmonary or respiratory tract inflammation in humans.

  本发明涉及化合物，其作为合成脂氧素A4类似物的中间体有用，该类似物的化学式为(I)和(II)，其中R1、R2、R3、R4和R5如本文所述。这些类似物对于治疗人体内的炎症和自身免疫性疾病有用。这些类似物也对于治疗人体内的肺部或呼吸道炎症有用。
• Novel 3-Oxa Lipoxin A₄ Analogues with Enhanced Chemical and Metabolic Stability Have Anti-inflammatory Activity in Vivo
  作者：William J. Guilford、John G. Bauman、Werner Skuballa、Shawn Bauer、Guo Ping Wei、David Davey、Caralee Schaefer、Cornell Mallari、Jennifer Terkelsen、Jih-Lie Tseng、Jun Shen、Babu Subramanyam、Arndt J. Schottelius、John F. Parkinson

  DOI：10.1021/jm030569l

  日期：2004.4.1

  Lipoxin A(4) (LXA(4)) is a structurally and functionally distinct natural product called an eicosanoid, which displays immunomodulatory and anti-inflammatory activity but is rapidly metabolized to inactive catabolites in vivo. A previously described analogue of LXA(4), methyl (5R,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate (2, ATLa), was shown to have a poor pharmacokinetic profile after both oral and intravenous administration, as well as sensitivity to acid and light. The chemical stability of the corresponding E,E,E-trien-11-yne analogue, 3, was improved over 2 without loss of efficacy in the mouse air pouch model of inflammation. Careful analysis of the plasma samples from the pharmacokinetic assays for both 2 and 3 identified a previously undetected metabolite, which is consistent with metabolism by beta-oxidation. The formation of the oxidative metabolites was eliminated with the corresponding 3-oxatetraene, 4, and the 3-oxatrien-11-yne, 5, analogues of 2. Evaluation of 3-oxa analogues 4 and 5 in calcium ionophore-induced acute skin inflammation model demonstrated similar topical potency and efficacy compared to 2. The 3-oxatrien-11-yne analogue, 5, is equipotent to 2 in an animal model of inflammation but has enhanced metabolic and chemical stability and a greatly improved pharmacokinetic profile.
• US7223798B2
  申请人：——

  公开号：US7223798B2

  公开（公告）日：2007-05-29
• US7994346B2
  申请人：——

  公开号：US7994346B2

  公开（公告）日：2011-08-09