12-(环己基氨基甲酰氨基)十二烷酸 | 479413-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 12-(环己基氨基甲酰氨基)十二烷酸
• 英文名称: CUDA
• 英文别名: 12-(3-cyclohexan-1-yl-ureido)-dodecanoic acid；12-(3-cyclohexan-1-yl-ureido)dodecanoic acid；12-[(Cyclohexylcarbamoyl)amino]dodecanoic acid；12-(cyclohexylcarbamoylamino)dodecanoic acid
• CAS: 479413-68-8
• 化学式: C₁₉H₃₆N₂O₃
• 分子量: 340.506
• InChiKey: HPTJABJPZMULFH-UHFFFAOYSA-N

物化性质

• 沸点：
  549.4±19.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• 溶解度：
  乙醇中≤1mg/ml；DMSO 中≤5mg/ml；二甲基甲酰胺中≤10mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

CUDA 是一种有效的可溶性环氧水解酶 (sEH) 抑制剂，对小鼠 sEH 和人 sEH 的 IC50 分别为 11.1 nM 和 112 nM。CUDA 能选择性地上调过氧化物酶体增殖激活受体 PPARalpha 的活性，并可能对心血管疾病的研究有价值。

靶点

	PPARα	mouse sEH	human sEH
IC50 (nM)	-	11.1	112

体外研究

CUDA（10 μM，18 小时）在 COS-7 细胞中可产生 PPARalpha 6 倍和 3 倍的增加。CUDA 不改变 PPARalpha 蛋白表达，并且竞争性抑制 Wy-14643（pirinixic acid）与 PPARalpha 的配体结合域相结合，表明它作为 PPARalpha 配体的功能。

Western Blot 分析

细胞系:	COS-7 细胞
浓度 (μM):	10
孵育时间 (小时):	18
结果:	激活 PPARα，与配体结合域结合。

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反应信息

• 作为产物：
  描述：

  环己基异氰酸酯 、 12-氨基十二酸 以 正己烷 为溶剂， 以72%的产率得到12-(环己基氨基甲酰氨基)十二烷酸
  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

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

  公开号：US20050164951A1

  公开（公告）日：2005-07-28

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

  提供了抑制可溶性环氧化酶（sEH）的抑制剂，这些抑制剂结合了多个药效团，在治疗疾病方面非常有用。
• INHIBITORS FOR THE SOLUBLE EPOXIDE HYDROLASE
  申请人：Hammock Bruce D.

  公开号：US20090326039A1

  公开（公告）日：2009-12-31

  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水解酶（sEH）的抑制剂，其中包含多个药效团。
• INHIBITORS OF EPOXIDE HYDROLASES FOR THE TREATMENT OF INFLAMMATION
  申请人：Hammock D. Bruce

  公开号：US20070117782A1

  公开（公告）日：2007-05-24

  The invention provides compounds that inhibit epoxide hydrolase in therapeutic applications for treating hypertension. A preferred class of compounds for practicing the invention have the structure shown by Formula 1 wherein Z is oxygen or sulfur, W is carbon phosphorous or sulfur, X and Y is each independently nitrogen, oxygen, or sulfur, and X can further be carbon, at least one of R 1 -R 4 is hydrogen, R 2 is hydrogen when X is nitrogen but is not present when X is sulfur or oxygen, R 4 is hydrogen when Y is nitrogen but is not present when Y is sulfur or oxygen, R 1 and R 3 is each independently C 1 -C 20 substituted or unsubstituted alkyl, cycloalkyl, aryl, acyl, or heterocyclic.

  本发明提供了一些化合物，用于治疗高血压的治疗应用中，抑制环氧水解酶。实施本发明的优选化合物类别具有由式1所示的结构，其中Z为氧或硫，W为碳、磷或硫，X和Y各自独立地为氮、氧或硫，而X还可以是碳，R1-R4中至少有一个是氢，当X为氮时，R2为氢，但当X为硫或氧时，R2不存在，当Y为氮时，R4为氢，但当Y为硫或氧时，R4不存在，而R1和R3各自独立地为C1-C20取代或未取代的烷基、环烷基、芳基、酰基或杂环基。
• ACYL PIPERIDINE INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：Hammock Bruce D.

  公开号：US20130143925A1

  公开（公告）日：2013-06-06

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

  提供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。