8-farnesyloxycoumarin | 1415658-75-1

• 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: 8-farnesyloxycoumarin
• 英文别名: 8-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one
• CAS: 1415658-75-1
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: PBXGBTJEFPNUPA-QZAMUAOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  8-甲氧基-2-氧代-2H-色烯-3-羧酸 在 aluminum (III) chloride 、 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 生成 8-farnesyloxycoumarin
  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

• <i>O</i> ‐prenylated carbostyrils as a novel class of 15‐lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment
  作者：Seyed Jamal Alavi、Amir Zebarjadi、Mahdi Hosseini Bafghi、Hossein Orafai、Hamid Sadeghian

  DOI：10.1111/cbdd.13944

  日期：2021.11

  prenyloxy coumarins. The results showed that position and length of the prenyl moiety play the important role in lipoxygenase inhibitory activity. Among all of the synthetic compounds (coumarin and carbostyril derivatives), 5-farnesyloxycoumarin and 8-farnesyloxycarbostyril demonstrated the best inhibitory activity by IC50 values of 1.1 µM and 0.53 µM, respectively.

  动物和植物中不饱和脂质的催化过氧化与 15-脂氧合酶的活性密切相关。众所周知，脂氧合酶 (LOX) 在许多急性和慢性综合征中发挥着重要作用，例如炎症、哮喘、癌症和过敏。在本研究中，合成了一系列单异戊二烯氧基喹啉，并评估其作为大豆15-脂氧合酶（SLO）的潜在抑制剂，并将其抑制效力与先前报道的单异戊二烯氧基香豆素进行了比较。合成化合物通过竞争机制抑制脂氧合酶，如异戊二烯氧基香豆素。结果表明异戊烯基部分的位置和长度在脂氧合酶抑制活性中起着重要作用。在所有合成化合物（香豆素和喹诺酮衍生物）中，5-法呢基氧基香豆素和8-法呢基氧基喹诺酮表现出最佳的抑制活性，IC 50值分别为1.1 µM 和0.53 µM。
• 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.