3-methoxy-2-methyl-5-[(methylamino)methyl]pyridin-4(1H)-one | 812653-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-2-methyl-5-[(methylamino)methyl]pyridin-4(1H)-one
• 英文别名: 3-methoxy-2-methyl-5-methylaminomethyl-1H-pyridin-4-one；3-Methoxy-2-methyl-5-[(methylamino)methyl]-1,4-dihydropyridin-4-one；3-methoxy-2-methyl-5-(methylaminomethyl)-1H-pyridin-4-one
• CAS: 812653-95-5
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: SMLJGBJJUOOBCT-UHFFFAOYSA-N

物化性质

• 熔点：
  99-108 °C
• 沸点：
  301.8±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-methyl-5-[(methylamino)methyl]pyridin-4(1H)-one 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到3-hydroxy-2-methyl-5-((methylamino)methyl)pyridin-4(1H)-one
  参考文献：
  名称：

  Macromolecular iron-chelators via RAFT-polymerization for the inhibition of methicillin-resistant Staphylococcus aureus growth

  摘要：

  A series of linear poly (glycidyl methacrylate) (PGMA) polymers were synthesized via RAFT polymerization and conjugated with amine-containing 3-hydroxypyridin-4-ones (HPOs) to generate a panel of HPO-containing materials with controlled structures and specific iron-binding functions. The structures of the resulting polymers were characterized via H-1 NMR, GPC and FT-IR and their chelating capacity for iron was investigated using UV-Vis spectrophotometric titration of the iron(III) complexes. In vitro antimicrobial studies of selected ligand-containing homopolymers demonstrate that the homopolymers are capable of inhibiting the growth of methicillin-resistant Staphylococcus aureus (MRSA). It is proposed that the inhibition activity of MRSA is derived from the iron-chelating capability of the iron-binding polymers. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2016.01.073
• 作为产物：
  描述：

  麦芽醇 在 palladium on activated charcoal 氢氧化钾 、 ammonium hydroxide 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 28.0h， 生成 3-methoxy-2-methyl-5-[(methylamino)methyl]pyridin-4(1H)-one
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s

文献信息

• Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors
  作者：Yongmin Ma、Wei Luo、Peter J. Quinn、Zudong Liu、Robert C. Hider

  DOI：10.1021/jm049751s

  日期：2004.12.1

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.
• The selective quantification of iron by hexadentate fluorescent probes
  作者：Yong Min Ma、Robert C. Hider

  DOI：10.1016/j.bmc.2009.09.052

  日期：2009.12

  The synthesis of four hexadentate fluorescent probes is described, where the fluorescent moiety is based on either coumarin or fluorescein and the chelating moiety is based on either 3-hydroxypyridin-4-one or 3-hydroxypyran-4-one. The fluorescence is quenched when the probe chelating moieties bind iron. The probes were found to be selective for iron over other metals such as Cu, Zn, Ni, Mn and Co. The effect of Cu on fluorescence quenching can be eliminated in the presence of N, N, N', N'-tetrakis(2-pyridylmethyl)-ethylenediamine. Competition studies demonstrate that the exchange of iron between pyridinone-based probes and apotransferrin is very slow. The ability to scavenge iron from oligomeric iron(III) citrate complexes demonstrate that the pyridinone probes scavenges iron faster than deferiprone and desferrioxamine. The fluorescence intensity of the fluorescein-based probe is quantitatively related to the iron concentration with the limit of detection being 10(8) M. (C) 2009 Elsevier Ltd. All rights reserved.
• Targeting the Lysosome: Fluorescent Iron(III) Chelators To Selectively Monitor Endosomal/Lysosomal Labile Iron Pools
  作者：Sarah Fakih、Maria Podinovskaia、Xiaole Kong、Helen L. Collins、Ulrich E. Schaible、Robert C. Hider

  DOI：10.1021/jm8001247

  日期：2008.8.1

  Iron-sensitive fluorescent chemosensors in combination with digital fluorescence spectroscopy have led to the identification of a distinct subcellular compartmentation of intracellular redox-active "labile" iron. To investigate the distribution of labile iron, our research has been focused on the development of fluorescent iron sensors targeting the endosomal/lysosomal system. Following the recent introduction of a series of 3-hydroxypyridin-4-one (HPO) based fluorescent probes we present here two novel HPO sensors capable of accumulating and monitoring iron exclusively in endosomal/lysosomal compartments. Flow cytometric and confocal microscopy studies in murine macrophages revealed endosomal/lysosomal sequestration of the probes and high responsiveness toward alterations of vesicular labile iron concentrations. This allowed assessment of cellular iron status with high sensitivity in response to the clinically applied medications desfenioxamine, deferiprone, and deferasirox. The probes represent a powerful class of sensors for quantitative iron detection and clinical real-time monitoring of subeellular labile iron levels in health and disease.
• Macromolecular iron-chelators via RAFT-polymerization for the inhibition of methicillin-resistant Staphylococcus aureus growth
  作者：Junpei Li、Eniola D. Olaleye、Xiaole Kong、Tao Zhou、Yongmin Ma、Jagoda Jurach、Osamah Al Rugaie、Robert C. Hider、Guoqing Zhang、Selwa Alsam、Vincenzo Abbate

  DOI：10.1016/j.polymer.2016.01.073

  日期：2016.3

  A series of linear poly (glycidyl methacrylate) (PGMA) polymers were synthesized via RAFT polymerization and conjugated with amine-containing 3-hydroxypyridin-4-ones (HPOs) to generate a panel of HPO-containing materials with controlled structures and specific iron-binding functions. The structures of the resulting polymers were characterized via H-1 NMR, GPC and FT-IR and their chelating capacity for iron was investigated using UV-Vis spectrophotometric titration of the iron(III) complexes. In vitro antimicrobial studies of selected ligand-containing homopolymers demonstrate that the homopolymers are capable of inhibiting the growth of methicillin-resistant Staphylococcus aureus (MRSA). It is proposed that the inhibition activity of MRSA is derived from the iron-chelating capability of the iron-binding polymers. (C) 2016 Elsevier Ltd. All rights reserved.