N-[3-prop-2-enyl-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]phenyl]cyclobutanecarboxamide | 1394965-62-8

• 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: N-[3-prop-2-enyl-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]phenyl]cyclobutanecarboxamide
• CAS: 1394965-62-8
• 化学式: C₂₉H₄₁NO₂
• 分子量: 435.65
• InChiKey: MNZUAUDHMPJMBV-JUDCTDMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  4-(烯丙氧基)苯胺 在 氢气 、 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 、 N,N-二乙基苯胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 18.75h， 生成 N-[3-prop-2-enyl-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]phenyl]cyclobutanecarboxamide
  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.