Tetradecanoic acid cyclohexylamide | 17427-95-1

• 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: Tetradecanoic acid cyclohexylamide
• 英文别名: N-cyclohexyltetradecanamide
• CAS: 17427-95-1
• 化学式: C₂₀H₃₉NO
• 分子量: 309.536
• InChiKey: OJHKIQNTPYAYMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Tetradecanoic acid cyclohexylamide 、 碘甲烷 在 sodium hydroxide 作用下， 生成 Tetradecanoic acid cyclohexyl-methyl-amide
  参考文献：
  名称：

  长烷基链酰胺，胺及其衍生物对犬round虫幼虫的杀线虫活性。

  摘要：

  检查了具有长烷基链的酰胺和胺对犬round虫第二阶段幼虫的杀线虫活性。在氮上具有较小取代基的长链酰基酰胺显示出更强的活性，环状胺酰胺的活性强于无环酰胺。在一系列同源酰胺中，活性取决于烷基链长：在最佳链长处达到最大值，而在较短和较长的同系物中均降低。通过使用双线性模型分析了同系物的活性与疏水性之间的关系。对于所有中性酰胺，提供最大活性的化合物的疏水性均相似，但分子中具有额外胺基的酰胺具有不同的值。具有长烷基链的叔胺及其盐也具有与相应酰胺相当的杀线虫活性。这些盐以低于其临界胶束浓度的浓度杀死幼虫，表明它们表现为杀线虫作用的单个分子。

  DOI：

  10.1248/cpb.40.3234
• 作为产物：
  描述：

  肉豆蔻酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 Tetradecanoic acid cyclohexylamide
  参考文献：
  名称：

  作为 N-肉豆蔻酰转移酶抑制剂的新型肉豆蔻酸衍生物的发现：设计、合成、分析、计算研究和抗真菌活性

  摘要：

  近年来，N-肉豆蔻酰转移酶（NMT）已被确定为治疗真菌感染的新靶点。据观察，目前真菌感染引起的发病率和死亡率有所增加。因此，通过分子对接研究和ADMET研究，以NMT（N-肉豆蔻酰转移酶）为靶点，设计了一系列新型肉豆蔻酸衍生物。通过将肉豆蔻酸转化为肉豆蔻酰氯并与芳基胺偶联生成相应的肉豆蔻酸衍生物来合成所设计的肉豆蔻酸衍生物。通过 FTIR、NMR 和 HRMS 光谱分析对化合物进行纯化和表征。在这项研究中，我们进行了目标 NMT 抑制测定。在NMT筛选试验结果中，化合物3u、3m和3t比其他肉豆蔻酸衍生物表现出更好的抑制作用。在体外抗真菌评估中，通过测定肉豆蔻酸衍生物的最低抑制浓度 (MIC50) 来评估其对白色念珠菌和黑曲霉菌株的作用。与标准药物FLZ（氟康唑）相比，化合物3u、3k、3r和3t对白色念珠菌表现出优异的抗真菌能力，化合物3u、3m和3r对黑曲霉表现出优异的抗真菌能力。总之，我们确定了一系列新的抗真菌剂。

  DOI：

  10.3390/antibiotics12071167

文献信息

• 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。
• 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.
• INHIBITORS OF EPOXIDE HYDROLASES FOR THE TREATMENT OF HYPERTENSION
  申请人：Kroetz Deanna L.

  公开号：US20110245331A1

  公开（公告）日：2011-10-06

  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.
• US8815951B2
  申请人：——

  公开号：US8815951B2

  公开（公告）日：2014-08-26
• Studies on Crude Drugs Effective on Visceral Larva Migrans. Part XVI. Nematocidal Activity of Long Alkyl Chain Amides, Amines, and Their Derivatives on Dog Roundworm Larvae.
  作者：Fumiyuki KIUCHI、Satomi NISHZAWA、Hiromi KAWANISHI、Sayuri KINOSHITA、Hisanao OHSIMA、Akiyo UCHITANI、Noriko SEKINO、Miki ISHIDA、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.3234

  日期：——

  activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached

  检查了具有长烷基链的酰胺和胺对犬round虫第二阶段幼虫的杀线虫活性。在氮上具有较小取代基的长链酰基酰胺显示出更强的活性，环状胺酰胺的活性强于无环酰胺。在一系列同源酰胺中，活性取决于烷基链长：在最佳链长处达到最大值，而在较短和较长的同系物中均降低。通过使用双线性模型分析了同系物的活性与疏水性之间的关系。对于所有中性酰胺，提供最大活性的化合物的疏水性均相似，但分子中具有额外胺基的酰胺具有不同的值。具有长烷基链的叔胺及其盐也具有与相应酰胺相当的杀线虫活性。这些盐以低于其临界胶束浓度的浓度杀死幼虫，表明它们表现为杀线虫作用的单个分子。