5-isopentenyloxycoumarin | 92190-32-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-isopentenyloxycoumarin
• 英文别名: 5-<3-Methyl-but-2-en-yloxy>-chromen-2-on；5-(3-Methyl-but-2-en-yloxy)-chromen-2-on；5-(3-Methylbut-2-enoxy)chromen-2-one
• CAS: 92190-32-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: IEHIAQSTRQUJGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2-羟基-6-甲氧基苯甲醛 在 aluminum (III) chloride 、 potassium carbonate 、 sodium hydrogensulfite 、 溶剂黄146 、 苯胺 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 24.0h， 生成 5-isopentenyloxycoumarin
  参考文献：
  名称：

  Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

  摘要：

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.006

文献信息

• Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors
  作者：Mehrdad Iranshahi、Atena Jabbari、Ala Orafaie、Robabeh Mehri、Soudabeh Zeraatkar、Taraneh Ahmadi、Maliheh Alimardani、Hamid Sadeghian

  DOI：10.1016/j.ejmech.2012.09.006

  日期：2012.11

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.