N-(3-allyl-4-(allyloxy)phenyl) adamantanecarboxamide | 1394965-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-allyl-4-(allyloxy)phenyl) adamantanecarboxamide
• 英文别名: N-(4-prop-2-enoxy-3-prop-2-enylphenyl)adamantane-1-carboxamide
• CAS: 1394965-54-8
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: RMZFJXJAFBOBMX-UHFFFAOYSA-N

物化性质

• 沸点：
  522.1±50.0 °C(predicted)
• 密度：
  1.136±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-allyloxy-4-nitrobenzene 在 tin(II) chloride dihdyrate 、 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 作用下， 以 二苯醚 、 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 18.08h， 生成 N-(3-allyl-4-(allyloxy)phenyl) adamantanecarboxamide
  参考文献：
  名称：

  Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

  摘要：

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.025

文献信息

• Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors
  作者：Atena Jabbari、Mahdieh Davoodnejad、Maliheh Alimardani、Amir Assadieskandar、Ali Sadeghian、Hadi Safdari、Jebraeel Movaffagh、Hamid Sadeghian

  DOI：10.1016/j.bmc.2012.07.025

  日期：2012.9

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.