2-(4-oxo-5-pentylcyclopent-2-en-1-yl) acetic acid | 1101843-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-oxo-5-pentylcyclopent-2-en-1-yl) acetic acid
• 英文别名: 4,5-didehydro-dihydrojasmonic acid；2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetic acid
• CAS: 1101843-12-2
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: MIIKBIRJDZKJEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-oxo-5-pentylcyclopent-2-en-1-yl) acetic acid 、 C.I.酸性橙108 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 25.0h， 以50%的产率得到N-(2-hydroxyethyl)-4,5-didehydro-dihydrojasmonylamide
  参考文献：
  名称：

  New jasmonate analogues as potential anti-inflammatory agents

  摘要：

  In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone ( 1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA(1), PGA(2), and 15-deoxy-Delta(12,14)-PGJ(2)). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that alpha-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.050
• 作为产物：
  描述：

  methyl 2-(4-oxo-5-pentylcyclopent-2-en-1-yl)acetate 在 porcine liver esterase 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 以80%的产率得到2-(4-oxo-5-pentylcyclopent-2-en-1-yl) acetic acid
  参考文献：
  名称：

  New jasmonate analogues as potential anti-inflammatory agents

  摘要：

  In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone ( 1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA(1), PGA(2), and 15-deoxy-Delta(12,14)-PGJ(2)). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that alpha-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.050