(1S,2R)-N-oleoylcyclopropanolamide | 1152704-90-9

• 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: (1S,2R)-N-oleoylcyclopropanolamide
• 英文别名: Cyclopropanolamide, 14b；(Z)-N-[(1S,2R)-2-hydroxycyclopropyl]octadec-9-enamide
• CAS: 1152704-90-9
• 化学式: C₂₁H₃₉NO₂
• 分子量: 337.546
• InChiKey: VCMSNKIQHBVCSW-XEWGXYBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-N-oleoylcyclopropanolamide 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 12.0h， 以1.2 mg的产率得到
  参考文献：
  名称：

  Conformationally Constrained Fatty Acid Ethanolamides as Cannabinoid and Vanilloid Receptor Probes

  摘要：

  To investigate if certain acylethanolamides bind to both cannabinoid (CB(1) and CB(2)) and vanilloid TRPV1 receptors because of their conformational flexibility, we introduced a methylene lock on their ethanolamine "head", thereby generating a cyclopropane ring with two stereogenic centers and chiral cis/trans diastereomers with different topology of presentation to binding sites. After resolution by chiral-phase HPLC, diastereo-and enantiopure arachidonoyl-, oleoyl-, and palmitoylcyclopropanolamides were tested in assays of CB(1), CB(2), and TRPV1 activity. Diastereodifferentiation between pairs of cis-trans isomers was observed only for TRPV1 activity, with poor enantiodifferentiation. Methylenation introduced (i) CB(1) receptor affinity in oleoylethanolamide while increasing in a diastereoselective way its activity at TRPV1 and (ii) strong diastereoselective activity at TRPV1, but not cannabinoid, receptors in the otherwise inactive palmitoylethanolamide. These results show that the N-alkyl group of acylethanolamides has a different role in their interaction with cannabinoid and vanilloid receptors and that acylcyclopropanolamides qualify as CB(1)/TRPV1 "hybrids" of potential therapeutic utility.

  DOI：

  10.1021/jm900130m