cis-2-[4-(4-fluoro-phenoxy)-cyclohexyl]-isoindole-1,3-dione | 885012-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: cis-2-[4-(4-fluoro-phenoxy)-cyclohexyl]-isoindole-1,3-dione
• 英文别名: cis-2-[4-(4-fluorophenoxy)cyclohexyl]isoindole-1,3-dione
• CAS: 885012-39-5
• 化学式: C₂₀H₁₈FNO₃
• 分子量: 339.366
• InChiKey: FCRCSKJINYHQDW-FZNQNYSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-2-[4-(4-fluoro-phenoxy)-cyclohexyl]-isoindole-1,3-dione 在 一水合肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Solid-phase combinatorial approach for the optimization of soluble epoxide hydrolase inhibitors

  摘要：

  A 192-member library of N,N'-disubstituted urea inhibitors was synthesized by a solid-phase method. The ureas were tested for their inhibitory activities against recombinant human soluble epoxide hydrolase. Simple carbocyclic or paralmeta-substituted phenyl groups showed inhibition potencies that were equal to or greater than adamantane-based sEH inhibitors, while the presence of bulky or ionizable groups close to the urea group dramatically decreased their activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.078
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 cis-2-[4-(4-fluoro-phenoxy)-cyclohexyl]-isoindole-1,3-dione
  参考文献：
  名称：

  Orally Bioavailable Potent Soluble Epoxide Hydrolase Inhibitors

  摘要：

  A series of N,N'-disubstituted ureas having a conformationally restricted cis- or traiis-1,4-cyclohexane alpha to the urea were prepared and tested as soluble epoxide hydrolase (sEH) inhibitors. This series of compounds showed low nanomolar to picomolar activities against recombinant human sEH. Both isomers showed similar potencies, but the trans isomers were more metabolically stable in human hepatic microsomes. Furthermore, these new potent inhibitors show a greater metabolic stability in vivo than previously described sEH inhibitors. We demonstrated that trans-4-[4-(3-adamantan-1-ylureido)cyclohexyloxy]benzoic acid 13g (t-AUCB, IC50 = 1.3 +/- 0.05 nM) had excellent oral bioavailability (98%, n = 2) and blood area under the curve in dogs and was effective in vivo to treat hypotension in lipopolysaccharide challenged murine models.

  DOI：

  10.1021/jm070270t

文献信息

• Inhibitors for the soluble epoxide hydrolase
  申请人：Hammock D. Bruce

  公开号：US20060270609A1

  公开（公告）日：2006-11-30

  Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

  提供了可用于治疗疾病的可溶性环氧酶（sEH）抑制剂，其中包含多个药效团。
• Inhibitors for the Soluble Epoxide Hydrolase
  申请人：HAMMOCK BRUCE D.

  公开号：US20110021448A1

  公开（公告）日：2011-01-27

  Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

  提供了可用于治疗疾病的可溶性环氧酶（sEH）抑制剂，其中包含多个药效团。
• [EN] IMPROVED INHIBITORS FOR THE SOLUBLE EPOXIDE HYDROLASE<br/>[FR] INHIBITEURS AMELIORES DE L'EPOXYDE HYDROLASE SOLUBLE
  申请人：UNIV CALIFORNIA

  公开号：WO2006045119A3

  公开（公告）日：2007-02-08
• IMPROVED INHIBITORS FOR THE SOLUBLE EPOXIDE HYDROLASE
  申请人：The Regents of the University of California

  公开号：EP1814875A2

  公开（公告）日：2007-08-08
• US7662910B2
  申请人：——

  公开号：US7662910B2

  公开（公告）日：2010-02-16