(2Z,4E)-N-(4-aminophenyl)-5-(1'-hydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z,4E)-N-(4-aminophenyl)-5-(1'-hydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienamide
• 英文别名: (2Z,4E)-N-(4-aminophenyl)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienamide
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: LGFUOUISOAJVEJ-POLRJCGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 、 对苯二胺 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到(2Z,4E)-N-(4-aminophenyl)-5-(1'-hydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienamide
  参考文献：
  名称：

  Synthesis, structural characterization and effect on human granulocyte intracellular cAMP levels of abscisic acid analogs

  摘要：

  The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i).We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2' and C-3' abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.035

文献信息

• Synthesis, structural characterization and effect on human granulocyte intracellular cAMP levels of abscisic acid analogs
  作者：Marta Bellotti、Annalisa Salis、Alessia Grozio、Gianluca Damonte、Tiziana Vigliarolo、Andrea Galatini、Elena Zocchi、Umberto Benatti、Enrico Millo

  DOI：10.1016/j.bmc.2014.11.035

  日期：2015.1

  The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i).We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2' and C-3' abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds. (C) 2014 Elsevier Ltd. All rights reserved.