sec-butyl 2-(4-methoxyphenyl)acetate | 1155174-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: sec-butyl 2-(4-methoxyphenyl)acetate
• 英文别名: Butan-2-yl 2-(4-methoxyphenyl)acetate
• CAS: 1155174-64-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: AVSIXWUNKFCTOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酸 、 2-溴丁烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以83%的产率得到sec-butyl 2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them

  摘要：

  A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC50 in SLO inhibition (IC50 = 3.8 and 1.9 mu M, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe-III-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.009

文献信息

• Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them
  作者：Hamid Sadeghian、Neda Attaran、Zeinab Jafari、Mohammad Reza Saberi、Mehdi Pordel、Mohammad Mahdi Riazi

  DOI：10.1016/j.bmc.2009.02.009

  日期：2009.3

  A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC50 in SLO inhibition (IC50 = 3.8 and 1.9 mu M, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe-III-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2009 Elsevier Ltd. All rights reserved.