(1S,5R)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-acetic acid | 123357-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-acetic acid
• 英文别名: 2-[(1S,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]acetic acid
• CAS: 123357-39-1
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: KJWUKJXAYNQYSS-HWKXXFMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1S,5R)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-acetic acid 、 三乙二醇 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 12.17h， 生成 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 4,5-dehydrojasmonate
  参考文献：
  名称：

  In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

  摘要：

  A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.052
• 作为产物：
  描述：

  benzyl 4,5-dehydrojasmonate 在 porcine liver esterase 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (1S,5R)-4-Oxo-5-(2Z)-2-penten-1-yl-2-cyclopentene-1-acetic acid
  参考文献：
  名称：

  In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates

  摘要：

  A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.052

文献信息

• In vitro stability and in vivo anti-inflammatory efficacy of synthetic jasmonates
  作者：Hung The Dang、Yoon Mi Lee、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Sun Mee Lee、Sang Kook Lee、Yuna Pyee、Hwa-Jin Chung、Hyung Ryong Moon、Hyung Sik Kim、Jee H. Jung

  DOI：10.1016/j.bmc.2012.04.052

  日期：2012.7

  A chlorinated methyl jasmonate analog (J7) was elaborated as an in vitro anti-inflammatory lead. However, its in vitro efficacy profile was not reproduced in a subsequent in vivo evaluation, presumably due to its rapid enzymatic hydrolysis in a biological system. In an attempt to improve the metabolic stability of the lead J7 by replacement of its labile methyl ester with reasonable ester groups, several analogs resistant to enzymatic hydrolysis were synthesized. In vivo evaluation of the stability-improved analogs showed that these compounds displayed higher efficacy than the lead J7, suggesting that these new jasmonate analogs may serve as potential anti-inflammatory leads. (C) 2012 Elsevier Ltd. All rights reserved.