methyl-6-nitroarachidonic acid | 1325718-40-8

• 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: methyl-6-nitroarachidonic acid
• 英文别名: AAMetNO2
• CAS: 1325718-40-8
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: BMTMLETXHNQWON-GGNMJIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  26.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  花生四烯酸甲酯 在 氮 、 硫酸 、 sodium nitrite 作用下， 以 正己烷 为溶剂， 反应 92.0h， 以5%的产率得到methyl-6-nitroarachidonic acid
  参考文献：
  名称：

  6-Methylnitroarachidonate: A novel esterified nitroalkene that potently inhibits platelet aggregation and exerts cGMP-mediated vascular relaxation

  摘要：

  Nitro-fatty acids represent endogenously occurring products of oxidant-induced nitration reactions. We have previously synthesized a mixture of four isomers of nitroarachidonic acid, a novel anti-inflammatory signaling mediator. In this study, we synthesized and chemically and biologically characterized for the first time an esterified nitroalkene derived from the nitration of methylarachidonate (AAMet): 6-methylnitroarachidonate (6-AAMetNO(2)). Synthesis was performed by reacting AAMet with sodium nitrite under acidic conditions. Analysis by mass spectrometry (positive-ion ESI-MS) showed an [M + H](+) ion of m/z 364, characteristic of AAMetNO(2). Fragmentation of this ion yielded a daughter ion at m/z 377, corresponding to the neutral loss of the nitro group ([M + H - HNO2](+)). Furthermore, IR signal at 1378 cm(-1) and NMR data confirmed the structure of a 6-nitro-positional isomer. This novel esterified nitroalkene was capable of promoting vascular protective actions including: (a) the induction of vasorelaxation via endothelium-independent mechanisms. associated with an increase in smooth muscle cell cGMP levels, and (b) a potent dose-dependent inhibition of human platelet aggregation. We postulate that 6-AAMetNO(2) could be a potential drug for the prevention of vascular and inflammatory diseases, and the presence of the methyl group may increase its pharmacological potential. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2010.11.031