7-geranyloxy-8-hydroxycoumarin | 562818-09-1

• 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: 7-geranyloxy-8-hydroxycoumarin
• 英文别名: 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-8-hydroxychromen-2-one
• CAS: 562818-09-1
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: DXTRQPVAXDUKQA-SDNWHVSQSA-N

物化性质

• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 7-geranyloxy-8-hydroxycoumarin 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以62%的产率得到7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-8-pentoxychromen-2-one
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of natural and semisynthetic geranyloxycoumarins

  摘要：

  Nine new 7-geranyloxycoumarin derivatives differently substituted at position 8 were semi-synthesised. Their topical anti-inflammatory activity was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Auraptene (7-geranytoxycoumarin), its 8-methoxy (collinin, 1) and 8-acetoxy derivatives (5) (1 mumol/cm(1)) provoked 50% oedema reduction, similarly to 0.25 mumol/cm(2) of the reference drug indomethacin, a nonsteroidal anti-inflammatory drug. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.009
• 作为产物：
  描述：

  邻苯三酚 在 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 反应 5.83h， 生成 7-geranyloxy-8-hydroxycoumarin
  参考文献：
  名称：

  加压二氧化碳中Collinin和isocollinin的溶解度：合成，溶解度参数和平衡测量

  摘要：

  Collinin是香豆素的衍生物，对癌症，结核病，牙周炎和其他普遍疾病显示出显着的潜力，通常从芸苔科植物中提取，收率很低。在这项工作中，通过两个平行的和两个连续的化学反应组成的途径，以不同的比例（从1至50 g前体）合成了collinin和本文称为异collinin的位置异构体。异构体的特征在于1 H NMR，131 H NMR，核Overhauser增强光谱NMR，熔融温度和熔融焓。对于每种异构体，通过在15种常见溶剂和两种溶剂混合物中的溶解度试验，通过实验确定Hansen溶解度参数及其溶解度球的半径。每种异构体的在加压CO溶解度2在30确定，并从72.2到112.9巴50℃，通过原位高压法技术，将其与蒽-CO验证2系统。在所考虑的温度和压力范围内，两种异构体在CO 2中的溶解度均随压力增加而增加，但在30和50°C时，Collinin分别表现出约80.8 bar和104.8 bar的渐近行为。

  DOI：

  10.1021/acs.jced.9b00234

文献信息

• Synthesis of Collinin, an Antiviral Coumarin
  作者：Massimo Curini、Francesco Epifano、Federica Maltese、Maria Carla Marcotullio、Sylvia Prieto Gonzales、Juan Carlos Rodriguez

  DOI：10.1071/ch02177

  日期：——

  Collinin (1), a geranyloxycoumarin, has been synthesized in three steps and 24.6% overall yield from pyrogallol (2) and propiolic acid (3).

  Collinin (1) 是一种香叶基氧基香豆素，由焦醛（2）和丙炔酸（3）经三个步骤合成，总收率为 24.6%。
• Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol
  作者：Giancarlo Cravotto、Stefano Chimichi、Bruna Robaldo、Marco Boccalini

  DOI：10.1016/j.tetlet.2003.09.114

  日期：2003.11

  Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by NOESY experiments; though less selectively, position 7 was also the most reactive in daphnetin (7,8-dihydroxycoumarin). The synthesis of the phytoestrogen ferujol is also reported for the first time. (C) 2003 Elsevier Ltd. All rights reserved.
• Strong antimicrobial activity of collinin and isocollinin against periodontal and superinfectant pathogens in vitro
  作者：Camilo Pardo-Castaño、Daniel Vásquez、Gustavo Bolaños、Adolfo Contreras

  DOI：10.1016/j.anaerobe.2020.102163

  日期：2020.4

  Periodontitis pathogenesis involves activation of host immune responses triggered by microbial dysbiosis. Therefore, controlling periodontal pathogens in-vivo is a main goal of periodontal therapy. New antimicrobials might help to control periodontal infection and improve treatment outcomes at "the dark times" of increasing antibiotic resistance. Here, we determined the biological activity of collinin and isocollinin against 8 bacterial strains. Antimicrobial activity of collinin and isocollinin, chlorhexidine digluconate (CHX) and sodium hypochlorite (NaClO) was evaluated against clinically relevant periodontal bacteria, like Aggregatibacter actinomycetemcomitans, Porphyromonas gingivalis, Fusobacterium nucleatum, Prevotella intermedia, Dialister pneumosintes strains and superinfectants like Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa strains. A broth microdilution test was carried out to determine the minimum inhibitory concentration of collinin and isocollinin against those strains, and bacterial viability was determined by resazurin assay at diverse concentration and exposure times. P. gingivalis was the most susceptible strain to collinin and isocollinin (MIC 2.1 mu g/mL and 4.2 mu g/mL respectively). Other periodontal pathogens showed MICs <17 mu g/mL for collinin and MICs between 20 and 42 mu g/mL for isocollinin, whereas CHX and NaClO showed MICs of 62 and 326 mu g/mL, respectively. Collinin and isocollinin also exhibited antimicrobial activity against superinfectant bacteria (MIC < 21 and <42 mu g/mL, respectively). Overall, collinin and isocollinin showed a remarkable antibacterial activity against relevant periodontal and superinfective bacteria, especially against P. gingivalis (MIC 2.1 mu g/mL and 4.2 mu g/mL respectively) and the highly virulent P. aeruginosa (MIC 5.2 and 20.8 mu g/mL, respectively). (C) 2020 Elsevier Ltd. All rights reserved.
• Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements
  作者：Camilo Pardo-Castaño、Andrés C. García、Paola Benavides、Gustavo Bolaños

  DOI：10.1021/acs.jced.9b00234

  日期：2019.9.12

  the Hansen solubility parameters and the radius of its solubility sphere were experimentally determined by solubility tests in 15 common solvents and two solvent blends. The solubility of each isomer in pressurized CO2 was determined at 30 and 50 °C from 72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique, which was validated with the anthracene–CO2 system. The solubility of both isomers

  Collinin是香豆素的衍生物，对癌症，结核病，牙周炎和其他普遍疾病显示出显着的潜力，通常从芸苔科植物中提取，收率很低。在这项工作中，通过两个平行的和两个连续的化学反应组成的途径，以不同的比例（从1至50 g前体）合成了collinin和本文称为异collinin的位置异构体。异构体的特征在于1 H NMR，131 H NMR，核Overhauser增强光谱NMR，熔融温度和熔融焓。对于每种异构体，通过在15种常见溶剂和两种溶剂混合物中的溶解度试验，通过实验确定Hansen溶解度参数及其溶解度球的半径。每种异构体的在加压CO溶解度2在30确定，并从72.2到112.9巴50℃，通过原位高压法技术，将其与蒽-CO验证2系统。在所考虑的温度和压力范围内，两种异构体在CO 2中的溶解度均随压力增加而增加，但在30和50°C时，Collinin分别表现出约80.8 bar和104.8 bar的渐近行为。
• Synthesis and anti-inflammatory activity of natural and semisynthetic geranyloxycoumarins
  作者：Massimo Curini、Francesco Epifano、Federica Maltese、Maria C Marcotullio、Aurelia Tubaro、Gianmario Altinier、Sylvia Prieto Gonzales、Juan C Rodriguez

  DOI：10.1016/j.bmcl.2004.02.009

  日期：2004.5

  Nine new 7-geranyloxycoumarin derivatives differently substituted at position 8 were semi-synthesised. Their topical anti-inflammatory activity was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Auraptene (7-geranytoxycoumarin), its 8-methoxy (collinin, 1) and 8-acetoxy derivatives (5) (1 mumol/cm(1)) provoked 50% oedema reduction, similarly to 0.25 mumol/cm(2) of the reference drug indomethacin, a nonsteroidal anti-inflammatory drug. (C) 2004 Elsevier Ltd. All rights reserved.