methyl 5-hydroxymethylene-jasmonate | 66971-95-7

• 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 5-hydroxymethylene-jasmonate
• 英文别名: opt.-inakt. (Z)-5-Hydroxymethylen-3-methoxycarbonylmethyl-2-(pent-2-enyl)-cyclopentanon
• CAS: 66971-95-7
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: BRDQLFQEKCPACT-CBHFCFCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxymethylene-jasmonate 在 吡啶 、 N,O-双(三氟乙酰基)羟胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以30%的产率得到methyl 5-cyano-jasmonate
  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：

  甲基茉莉酸酯 、 甲酸乙酯 在 甲醇 、 sodium hydride 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 反应 12.17h， 生成 methyl 5-hydroxymethylene-jasmonate
  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

文献信息

• Partial Syntheses of Methyl Dehydrojasmonate and Tuberolactone
  作者：Paul Dubs、Rita Stüssi

  DOI：10.1002/hlca.19780610308

  日期：1978.4.19

  The natural products methyl dehydrojasmonate (1) and tuberolactone (2) have been synthesized from methyl jasmonate (3) and jasmolactone (4) resp., via sulfenylation-sulfoxide pyrolysis.

  天然产物甲基dehydrojasmonate（1）和tuberolactone（2）从茉莉酮酸甲酯（已被合成3）和jasmolactone（4）RESP。，经由亚磺酰亚砜热解。