4-[(2S,3R)-3-(((E)-(2S,3S)-3-hydroxy-2-((Z)-oct-2-enyl)-5-oxocyclopentylidene)methyl)oxiran-2-yl]butanoic acid | 1477980-76-9

• 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: 4-[(2S,3R)-3-(((E)-(2S,3S)-3-hydroxy-2-((Z)-oct-2-enyl)-5-oxocyclopentylidene)methyl)oxiran-2-yl]butanoic acid
• 英文别名: 4-[(2S,3S)-3-[(E)-[(2S,3R)-3-hydroxy-2-[(Z)-oct-2-enyl]-5-oxocyclopentylidene]methyl]oxiran-2-yl]butanoic acid
• CAS: 1477980-76-9
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: HHCKGRLRYHXQJS-SYMNNRNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,4R)-1-acetyloxy-4-(4-methoxyphenylmethoxy)cyclopent-2-ene 在 sodium chlorite 、 甲酸 、 sodium dihydrogenphosphate dihydrate 、 溴 、 叔丁基锂 、 sodium hexamethyldisilazane 、 四氯化钛 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 正戊烷 为溶剂， 反应 12.83h， 生成 4-[(2S,3R)-3-(((E)-(2S,3S)-3-hydroxy-2-((Z)-oct-2-enyl)-5-oxocyclopentylidene)methyl)oxiran-2-yl]butanoic acid
  参考文献：
  名称：

  An Epoxyisoprostane Is a Major Regulator of Endothelial Cell Function

  摘要：

  The goal of these studies was to determine the effect of 5,6-epoxyisoprostane, El, on human aortic endothelial cells (HAEC). El can form as a phospholipase product of 1-palmitoyl-2-(5,6-epoxyisoprostane E2)-sn-glycero-3-phosphocholine, PEIPC, a proinflammatory molecule that accumulates in sites of inflammation where phospholipases are also increased. To determine the effect of El on HAEC, we synthesized several stereoisomers of El using a convergent approach from the individual optically pure building blocks, the epoxyaldehydes 5 and 6 and the bromoenones 14 and 16. The desired stereoisomer of El can be prepared from these materials in only six operations, and thus, large amounts of the product can be obtained. The trans/trans isomers had the most potent activity, suggesting specificity in the interaction of El with the cell surface. El has potent anti-inflammatory effects in HAEC. El strongly inhibits the production of MCP-1, a major monocyte chemotactic factor, and either decreases or minimally increases the levels of 10 proinflammatory molecules increased by PEIPC. El also strongly down-regulates the inflammatory effects of IL-1 beta, a major inflammatory cytokine. Thus El, a hydrolytic product of PEIPC, has potent anti-inflammatory function.

  DOI：

  10.1021/jm400959q

文献信息

• An Epoxyisoprostane Is a Major Regulator of Endothelial Cell Function
  作者：Wei Zhong、James R. Springstead、Ramea Al-Mubarak、Sangderk Lee、Rongsong Li、Benjamin Emert、Judith A. Berliner、Michael E. Jung

  DOI：10.1021/jm400959q

  日期：2013.11.14

  The goal of these studies was to determine the effect of 5,6-epoxyisoprostane, El, on human aortic endothelial cells (HAEC). El can form as a phospholipase product of 1-palmitoyl-2-(5,6-epoxyisoprostane E2)-sn-glycero-3-phosphocholine, PEIPC, a proinflammatory molecule that accumulates in sites of inflammation where phospholipases are also increased. To determine the effect of El on HAEC, we synthesized several stereoisomers of El using a convergent approach from the individual optically pure building blocks, the epoxyaldehydes 5 and 6 and the bromoenones 14 and 16. The desired stereoisomer of El can be prepared from these materials in only six operations, and thus, large amounts of the product can be obtained. The trans/trans isomers had the most potent activity, suggesting specificity in the interaction of El with the cell surface. El has potent anti-inflammatory effects in HAEC. El strongly inhibits the production of MCP-1, a major monocyte chemotactic factor, and either decreases or minimally increases the levels of 10 proinflammatory molecules increased by PEIPC. El also strongly down-regulates the inflammatory effects of IL-1 beta, a major inflammatory cytokine. Thus El, a hydrolytic product of PEIPC, has potent anti-inflammatory function.