N-(4-(allyloxy)phenyl)-4-methoxybenzamide | 881549-09-3

• 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-(4-(allyloxy)phenyl)-4-methoxybenzamide
• 英文别名: 4-methoxy-N-[4-(prop-2-en-1-yloxy)phenyl]benzamide；4-methoxy-N-(4-prop-2-enoxyphenyl)benzamide
• CAS: 881549-09-3
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: MZKKVNBOPZHMQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(烯丙氧基)苯胺 、 对甲氧基苯甲酰氯 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 N-(4-(allyloxy)phenyl)-4-methoxybenzamide
  参考文献：
  名称：

  Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors

  摘要：

  A group of 4-allyloxyaniline amides 5a-o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC(50) in SLO inhibition (IC(50) = 0.67 +/- 0.06 mu M). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe(3+)-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His(513) and Gln(716). It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.065

文献信息

• Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors
  作者：Seyed Mohammad Seyedi、Zeinab Jafari、Neda Attaran、Hamid Sadeghian、Mohammad Reza Saberi、Mohammad Mahdi Riazi

  DOI：10.1016/j.bmc.2008.12.065

  日期：2009.2

  A group of 4-allyloxyaniline amides 5a-o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC(50) in SLO inhibition (IC(50) = 0.67 +/- 0.06 mu M). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe(3+)-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His(513) and Gln(716). It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.