(R,5Z,8Z,11Z,14Z)-N-(1-hydroxypropan-2-yl)-16-phenylhexadeca-5,8,11,14-tetraenamide | 1097197-63-1

• 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: (R,5Z,8Z,11Z,14Z)-N-(1-hydroxypropan-2-yl)-16-phenylhexadeca-5,8,11,14-tetraenamide
• 英文别名: (5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]-16-phenylhexadeca-5,8,11,14-tetraenamide
• CAS: 1097197-63-1
• 化学式: C₂₅H₃₅NO₂
• 分子量: 381.558
• InChiKey: FFQDIJKWWKFNQV-CYKTZUFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  D-氨基丙醇 、 methyl (5Z,8Z,11Z,14Z)-16-phenylhexadeca-5,8,11,14-tetraenoate 在 sodium cyanide 作用下， 以 甲醇 为溶剂， 以74%的产率得到(R,5Z,8Z,11Z,14Z)-N-(1-hydroxypropan-2-yl)-16-phenylhexadeca-5,8,11,14-tetraenamide
  参考文献：
  名称：

  Development of novel tail-modified anandamide analogs

  摘要：

  To explore the hydrophobic groove subsite within the CB1 cannabinoid receptor we have designed and synthesized a group of tail-substituted anandamide analogs. Our design involves the introduction of aryl or heterocyclic ring as terminal substituents that are connected to the last cis-arachidonyl double bond through aliphatic chains of variable lengths. Our results indicate that there are strict stereochemical requirements for the interaction of such analogs with the CB1 receptor. The optimal pharmacophore includes the phenyl, p-substituted phenyl, or 3-furyl substituents attached to the cis-double bond through a four methylene chain. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.07.110

文献信息

• Development of novel tail-modified anandamide analogs
  作者：Fenmei Yao、Chen Li、Subramanian K. Vadivel、Anna L. Bowman、Alexandros Makriyannis

  DOI：10.1016/j.bmcl.2008.07.110

  日期：2008.11

  To explore the hydrophobic groove subsite within the CB1 cannabinoid receptor we have designed and synthesized a group of tail-substituted anandamide analogs. Our design involves the introduction of aryl or heterocyclic ring as terminal substituents that are connected to the last cis-arachidonyl double bond through aliphatic chains of variable lengths. Our results indicate that there are strict stereochemical requirements for the interaction of such analogs with the CB1 receptor. The optimal pharmacophore includes the phenyl, p-substituted phenyl, or 3-furyl substituents attached to the cis-double bond through a four methylene chain. Published by Elsevier Ltd.