N-arachidonoyl glycinal | 1125514-65-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N-arachidonoyl glycinal
• 英文别名: n-Arachidonoyl glycinal；(5Z,8Z,11Z,14Z)-N-(2-oxoethyl)icosa-5,8,11,14-tetraenamide
• CAS: 1125514-65-9
• 化学式: C₂₂H₃₅NO₂
• 分子量: 345.525
• InChiKey: OZYJHDYKUVDCHJ-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2,3-dihydroxypropyl)arachidonamide 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 以70%的产率得到N-arachidonoyl glycinal
  参考文献：
  名称：

  Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals

  摘要：

  N-Arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.087

文献信息

• [EN] NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] NOUVEAUX INHIBITEURS DE TRANSPORT DE GLYCINE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：UNIV SYDNEY

  公开号：WO2018132876A1

  公开（公告）日：2018-07-26

  The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.

  本发明涉及新型甘氨酸转运抑制剂化合物及其用于治疗疼痛的用途。
• Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals
  作者：Halikhedkar Aneetha、David K. O’Dell、Bo Tan、J. Michael Walker、Thomas D. Hurley

  DOI：10.1016/j.bmcl.2008.10.087

  日期：2009.1

  N-Arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. (C) 2008 Elsevier Ltd. All rights reserved.