N-cyclohexylurea-N'-hexanoic acid | 479413-50-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-cyclohexylurea-N'-hexanoic acid
• 英文别名: 6-{[(Cyclohexylamino)carbonyl]amino}hexanoic acid；6-(cyclohexylcarbamoylamino)hexanoic acid
• CAS: 479413-50-8
• 化学式: C₁₃H₂₄N₂O₃
• mdl: MFCD09734446
• 分子量: 256.345
• InChiKey: KFTVEPYSUSWBRD-UHFFFAOYSA-N

物化性质

• 沸点：
  499.6±24.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cyclohexylurea-N'-hexanoic acid 在 4-二甲氨基吡啶 、 氢氧化钾 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-2-(6-(3-cyclohexylureido)hexanamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  Peptidyl-urea based inhibitors of soluble epoxide hydrolases

  摘要：

  We prepared a series of amino acid derived cyclohexyl and adamantyl ureas and tested them as inhibitors of the human soluble epoxide hydrolase, and obtained very potent compounds (K-I = 15 nM) that are > 10-fold more soluble than previously described sEH inhibitors. While our lead compound 2 showed low apparent bioavailability in dogs and rats, this series of compounds revealed that sEH inhibitor structures could accept large groups that could lead to better orally available drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.073
• 作为产物：
  描述：

  环己基异氰酸酯 、 6-氨基己酸 以 正己烷 为溶剂， 以92%的产率得到N-cyclohexylurea-N'-hexanoic acid
  参考文献：
  名称：

  Structural refinement of inhibitors of urea-based soluble epoxide hydrolases

  摘要：

  The soluble epoxide hydrolase (sEH) is involved in the metabolism of arachidonic, linoleic, and other fatty acid epoxides, endogenous chemical mediators that play an important role in blood pressure regulation and inflammation. 1,3-Disubstituted ureas, carbamates, and amides are new potent and stable inhibitors of sEH. However, the poor solubility of the lead compounds limits their use. Inhibitor structure-activity relationships were investigated to better define the structural requirements for inhibition and to identify points in the molecular topography that could accept polar groups without diminishing inhibition potency. Results indicate that lipophilicity is an important factor controlling inhibitor potency. Polar groups could be incorporated into one of the alkyl groups without loss of activity if they were placed at a sufficient distance from the urea function. The resulting compounds had a 2-fold higher water solubility. These findings will facilitate the rational design and optimization of sEH inhibitors with better physical properties. (C) 2002 Published by Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(02)00952-8

文献信息

• Structural refinement of inhibitors of urea-based soluble epoxide hydrolases
  作者：Christophe Morisseau、Marvin H. Goodrow、John W. Newman、Craig E. Wheelock、Deanna L. Dowdy、Bruce D. Hammock

  DOI：10.1016/s0006-2952(02)00952-8

  日期：2002.5

  The soluble epoxide hydrolase (sEH) is involved in the metabolism of arachidonic, linoleic, and other fatty acid epoxides, endogenous chemical mediators that play an important role in blood pressure regulation and inflammation. 1,3-Disubstituted ureas, carbamates, and amides are new potent and stable inhibitors of sEH. However, the poor solubility of the lead compounds limits their use. Inhibitor structure-activity relationships were investigated to better define the structural requirements for inhibition and to identify points in the molecular topography that could accept polar groups without diminishing inhibition potency. Results indicate that lipophilicity is an important factor controlling inhibitor potency. Polar groups could be incorporated into one of the alkyl groups without loss of activity if they were placed at a sufficient distance from the urea function. The resulting compounds had a 2-fold higher water solubility. These findings will facilitate the rational design and optimization of sEH inhibitors with better physical properties. (C) 2002 Published by Elsevier Science Inc.
• Peptidyl-urea based inhibitors of soluble epoxide hydrolases
  作者：Christophe Morisseau、John W. Newman、Hsing-Ju Tsai、Preston A. Baecker、Bruce D. Hammock

  DOI：10.1016/j.bmcl.2006.07.073

  日期：2006.10

  We prepared a series of amino acid derived cyclohexyl and adamantyl ureas and tested them as inhibitors of the human soluble epoxide hydrolase, and obtained very potent compounds (K-I = 15 nM) that are > 10-fold more soluble than previously described sEH inhibitors. While our lead compound 2 showed low apparent bioavailability in dogs and rats, this series of compounds revealed that sEH inhibitor structures could accept large groups that could lead to better orally available drugs. (c) 2006 Elsevier Ltd. All rights reserved.