2-oxo-10(Z)-nonadecenamide

• 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: 2-oxo-10(Z)-nonadecenamide
• 英文别名: 2-Oxononadec-10-enamide；(Z)-2-oxononadec-10-enamide
• 化学式: C₁₉H₃₅NO₂
• 分子量: 309.492
• InChiKey: KNAHINXNTGMGLG-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydroxy-10(Z)-nonadecenoic acid 在 ammonium hydroxide 、 草酰氯 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-oxo-10(Z)-nonadecenamide
  参考文献：
  名称：

  Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide

  摘要：

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.

  DOI：

  10.1021/ja954064z

文献信息

• INHIBITORS OF OLEAMIDE HYDROLASE
  申请人：The Scripps Research Institute

  公开号：EP0910561B1

  公开（公告）日：2004-04-07
• US5856537A
  申请人：——

  公开号：US5856537A

  公开（公告）日：1999-01-05
• US6096784A
  申请人：——

  公开号：US6096784A

  公开（公告）日：2000-08-01
• [EN] OLEAMIDE IN EPILEPSY<br/>[FR] UTILISATION DE L'OLEAMIDE DANS LE TRAITEMENT DE L'EPILEPSIE
  申请人：UNIV SUNDERLAND

  公开号：WO2001035939A2

  公开（公告）日：2001-05-25

  There is described a method of treating a convulsant disorder which comprises altering the levels of oleamide in the brain of a patient suffering from such a disorder. The method may comprise altering the oleamide levels by administering a therapeutically effective amount of an amido hydrolase inhibitor, thus preventing the degradation of endogenous oleamide. Alternatively, the method may comprise administering a therapeutically effective amount of oleamide itself.
• Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid <i>cis</i>-9-Octadecenamide
  作者：Jean E. Patterson、Ian R. Ollmann、Benjamin F. Cravatt、Dale L. Boger、Chi -Huey Wong、Richard A. Lerner

  DOI：10.1021/ja954064z

  日期：1996.1.1

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.