4-methyl-7-(4-(bromomethyl)benzyloxy)coumarin | 898806-81-0

• 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: 4-methyl-7-(4-(bromomethyl)benzyloxy)coumarin
• 英文别名: 4-(4-methylcoumarin-7-yl-oxymethyl)benzylbromide；7-(4-bromomethylbenzyloxy)-4-methylcoumarin；7-[[4-(Bromomethyl)phenyl]methoxy]-4-methyl-chromen-2-one；7-[[4-(bromomethyl)phenyl]methoxy]-4-methylchromen-2-one
• CAS: 898806-81-0
• 化学式: C₁₈H₁₅BrO₃
• 分子量: 359.219
• InChiKey: QBGIPCUNEACMAV-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  509.3±50.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-7-(4-(bromomethyl)benzyloxy)coumarin 在 盐酸 、 potassium carbonate 作用下， 以 乙醚 、 氯仿 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 4-methyl-7-[[4-(1H-1,2,4-triazol-2-ium-2-ylmethyl)phenyl]methoxy]chromen-2-one;chloride
  参考文献：
  名称：

  一类新型潜在香豆素三唑衍生物的合成与评价

  摘要：

  设计，合成和评估了一系列新的基于香豆素的1,2,4-三唑衍生物，它们在体外对四种革兰氏阳性细菌（金黄色葡萄球菌，MRSA，枯草芽孢杆菌和黄球微球菌），四种革兰氏阴性细菌具有体外抗菌活性。细菌（大肠杆菌，寻常变形杆菌，伤寒沙门氏菌和痢疾志贺菌）以及三种真菌（白色念珠菌，酿酒酵母和烟曲霉）。）的两倍连续稀释技术。生物活性测定表明，与参考药物依诺沙星，绿霉素和氟康唑相比，一些合成的香豆素三唑显示出相当甚至更好的抗菌和抗真菌功效。香豆素双三唑化合物显示出比其相应的单三唑衍生物更强的抗菌和抗真菌功效。

  DOI：

  10.1016/j.bmcl.2010.12.059
• 作为产物：
  描述：

  间苯二酚 在 草酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4-methyl-7-(4-(bromomethyl)benzyloxy)coumarin
  参考文献：
  名称：

  一类新型潜在香豆素三唑衍生物的合成与评价

  摘要：

  设计，合成和评估了一系列新的基于香豆素的1,2,4-三唑衍生物，它们在体外对四种革兰氏阳性细菌（金黄色葡萄球菌，MRSA，枯草芽孢杆菌和黄球微球菌），四种革兰氏阴性细菌具有体外抗菌活性。细菌（大肠杆菌，寻常变形杆菌，伤寒沙门氏菌和痢疾志贺菌）以及三种真菌（白色念珠菌，酿酒酵母和烟曲霉）。）的两倍连续稀释技术。生物活性测定表明，与参考药物依诺沙星，绿霉素和氟康唑相比，一些合成的香豆素三唑显示出相当甚至更好的抗菌和抗真菌功效。香豆素双三唑化合物显示出比其相应的单三唑衍生物更强的抗菌和抗真菌功效。

  DOI：

  10.1016/j.bmcl.2010.12.059

文献信息

• Non-conjugated dendrimers with a porphyrin core and coumarin chromophores as peripheral units: Synthesis and photophysical properties
  作者：Mao Mao、Qin-Hua Song

  DOI：10.1016/j.dyepig.2011.08.020

  日期：2012.3

  absorption spectrum of porphyrin core and the emission spectrum of the coumarin moiety results in high energy-transfer efficiency. Secondly, a long alkyl side-chain improves solubility of dendrimers, but also prevents the coumarins from self-quenching. Hence, the dendrimer with N-octyl groups possesses a higher efficiency than that with N-ethyl groups. The dendrimers emit red light with higher fluorescence

  合成并表征了三种以非共性香豆素为树枝状的卟啉核树枝状聚合物。通过UV / Vis吸收和荧光光谱在稀CH 2 Cl 2溶液和纯净薄膜中研究标题化合物的光物理性质。从香豆素单元到卟啉核心的分子内能量转移清楚地揭示了影响能量转移效率的两个因素。首先，卟啉核心的吸收光谱与香豆素部分的发射光谱之间更好的光谱重叠导致高的能量转移效率。其次，长的烷基侧链提高了树枝状聚合物的溶解度，但也阻止了香豆素的自猝灭。因此，具有N的树枝状大分子辛基的效率要高于N乙基。树枝状聚合物发出的红光比游离卟啉具有更高的荧光量子产率。
• Poly(aryl ether) Dendritic Structures Based on 1,4,8,11-Tetraazacyclotetradecane Core: Synthesis, Characterization, Photophysical Properties and Biological activity
  作者：M. Dilek、O. Dilek Bayindir

  DOI：10.14233/ajchem.2015.18414

  日期：——

  This work describes the synthesis of two new dendrimers consisting of a 1,4,8,11-tetraazacyclotetradecane (cyclam) core appended with poly(aryl ether) dendritic structures carrying a donor (4-methyl-7-hydroxycoumarin) on the surface. Its structure was determined by 1H NMR, 13C NMR and elemental analysis. The photophysical properties of the series of poly(aryl ether) dendrimers have been determined and the effect of the generation number on the absorption and emission properties of the synthesized dendritic structures was investigated. As the chromophore group number on the surface of the dendritic structure increased, molar absorptivity coefficients and emission intensities of the structures were found to increase. The prepared dendritic structures were tested for their antimicrobial activity against, Salmonella typhimurium NRRLB, Micrococcus luteus, Pseudomonas aeruginosa, Enterococcus fecalis ATCC-29212, Bacillus cereus ATCC-117787, Klepsiella pneumonia, Bacillus subtilis NRS-744, Proteus vulgoris, Yersinia enterolitica and Saccharomyces cereviciae. Synthesized dendritic structures showed moderate activity against different strains of bacteria.

  这项工作描述了两种新型树枝状大分子的合成，它们的核心是由1,4,8,11-四氮杂环十四烷（cyclam）组成，其表面附有带有供体（4-甲基-7-羟基香豆素）的多（芳基醚）树枝状结构。其结构通过1H NMR、13C NMR和元素分析确定。已经确定了这一系列多（芳基醚）树枝状大分子的光物理性质，并研究了代数对合成树枝状结构吸收和发射性质的影响。随着树枝状结构表面色团数量的增加，发现这些结构的摩尔吸收系数和发射强度也随之增加。制备的树枝状结构被测试了它们对以下微生物的抗菌活性：鼠伤寒沙门氏菌NRRLB、藤黄微球菌、绿脓杆菌、粪肠球菌ATCC-29212、蜡样芽孢杆菌ATCC-117787、肺炎克雷伯菌、枯草芽孢杆菌NRS-744、普通变形杆菌、耶尔森氏菌小肠结肠炎和酿酒酵母。合成的树枝状结构对不同细菌株显示出中等的活性。
• Structure-Based Design and Optimization of Multitarget-Directed 2<i>H</i>-Chromen-2-one Derivatives as Potent Inhibitors of Monoamine Oxidase B and Cholinesterases
  作者：Roberta Farina、Leonardo Pisani、Marco Catto、Orazio Nicolotti、Domenico Gadaleta、Nunzio Denora、Ramon Soto-Otero、Estefania Mendez-Alvarez、Carolina S. Passos、Giovanni Muncipinto、Cosimo D. Altomare、Alessandra Nurisso、Pierre-Alain Carrupt、Angelo Carotti

  DOI：10.1021/acs.jmedchem.5b00599

  日期：2015.7.23

  The multifactorial nature of Alzheimer's disease calls for the development of multitarget agents addressing key pathogenic processes. To this end, by following a docking-assisted hybridization strategy, a number of aminocoumarins were designed, prepared, and tested as monoamine oxidases (MAOs) and acetyl- and butyryl-cholinesterase (AChE and BChE) inhibitors. Highly flexible N-benzyl-N-alkyloxy coumarins 2-12 showed good inhibitory activities at MAO-B, AChE, and BChE but low selectivity. More rigid inhibitors, bearing meta-and para-xylyl linkers, displayed: good inhibitory activities and high MAO-B selectivity. Compounds 21, 24, 37, and 39, the last two featuring art improved hydrophilic/lipophilic balance, exhibited excellent activity profiles with nanomolar inhibitory potency toward hMAO-B, high hMAO-B over hMAO-A selectivity and submicromolar potency at hAChE. Cell-based assays of BBB permeation, neurotoxicity, and neuroprotection supported the potential of compound 37 as a BBB-permeant neuroprotective agent against H2O2-induced oxidative stress with poor interaction as P-gp substrate and very low cytotoxicity.
• Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents
  作者：Yuan Shi、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2010.12.059

  日期：2011.2

  A series of new coumarin-based 1,2,4-triazole derivatives were designed, synthesized and evaluated for their antimicrobial activities in vitro against four Gram-positive bacteria (Staphylococcus aureus, MRSA, Bacillus subtilis and Micrococcus luteus), four Gram-negative bacteria (Escherichia coli, Proteus vulgaris, Salmonella typhi and Shigella dysenteriae) as well as three fungi (Candida albicans

  设计，合成和评估了一系列新的基于香豆素的1,2,4-三唑衍生物，它们在体外对四种革兰氏阳性细菌（金黄色葡萄球菌，MRSA，枯草芽孢杆菌和黄球微球菌），四种革兰氏阴性细菌具有体外抗菌活性。细菌（大肠杆菌，寻常变形杆菌，伤寒沙门氏菌和痢疾志贺菌）以及三种真菌（白色念珠菌，酿酒酵母和烟曲霉）。）的两倍连续稀释技术。生物活性测定表明，与参考药物依诺沙星，绿霉素和氟康唑相比，一些合成的香豆素三唑显示出相当甚至更好的抗菌和抗真菌功效。香豆素双三唑化合物显示出比其相应的单三唑衍生物更强的抗菌和抗真菌功效。