3-hydroxy-2-methyl-1-(naphthalene-1-yl)pyridin-4(1H)-one | 1256698-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxy-2-methyl-1-(naphthalene-1-yl)pyridin-4(1H)-one
• 英文别名: 3-Hydroxy-2-methyl-1-naphthalen-1-ylpyridin-4-one；3-hydroxy-2-methyl-1-naphthalen-1-ylpyridin-4-one
• CAS: 1256698-61-9
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: KWLRWSAEOLQKDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-methyl-1-(naphthalene-1-yl)pyridin-4(1H)-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以60%的产率得到3-hydroxy-2-methyl-1-(naphthalene-1-yl)pyridine-4(1H)-thione
  参考文献：
  名称：

  新型水溶性基于硫代吡啶酮的有机金属配合物及其意外（生物学）行为库的合成，修饰和生物学评估。

  摘要：

  合成和表征了一系列16种具有优异水溶性，增加的稳定性和显着的细胞毒性的双核硫代吡啶酮基有机金属。这项工作的配合物形成了二聚体，在极性质子溶剂中具有双正电荷，这说明它们在水溶液中的出色溶解性。它们中的大多数显示出比其亲本硫代麦芽酚复合物更高的抗增殖活性，取决于所采用的金属中心，配体修饰和细胞系，其具有出乎意料的细胞毒性趋势。通过氨基酸相互作用研究，3D球体模型中的细胞毒性测试，激光消融，细胞蓄积测量以及细胞周期实验，收集了它们在生物系统中行为的见解。

  DOI：

  10.1002/chem.201905546
• 作为产物：
  描述：

  3-hydroxy-2-methyl-1-naphthyl-4-pyridinone hydrochloride 在 sodium carbonate 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 以100%的产率得到3-hydroxy-2-methyl-1-(naphthalene-1-yl)pyridin-4(1H)-one
  参考文献：
  名称：

  Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor

  摘要：

  Two novel 3-hydroxy-4-pyridinone/naphthalene conjugates (L1 and L2) with different distances between the chelating and the fluorescent moieties were synthesized using conventional heating and microwave irradiation achieving a shorter reaction time. The structure of both compounds was confirmed by X-ray crystallography, revealing that these compounds were isolated as hydrochloride salts in dihydroxypyridinium forms. In solution and in the presence of a base, the tautomeric keto forms may be obtained as it was elucidated by NMR analysis. The dihydroxypyridinium form of L1 exhibits fluorescence at 450 nm, both in ACN and DMSO, whereas the corresponding keto form exhibits fluorescence at 365 nm. In contrast, the dihydroxypyridinium form of L2 only fluoresces in DMSO, exhibiting a band at 340 nm, while the keto form is non-fluorescent. These distinct fluorescent behaviors reveal that the tautomeric form in which the ligands are isolated and the distance between the chelating and fluorescent functions strongly influences their fluorescence properties. Ligand L1 exhibits better fluorescence properties and its fluorescence intensity is quenched in the presence of variable concentration of Cu2+, Zn2+, and Fe3+, thus making it suitable to be used as ion sensor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.065

文献信息

• Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor
  作者：Ana M.G. Silva、Andreia Leite、Mariana Andrade、Paula Gameiro、Paula Brandão、Vítor Felix、Baltazar de Castro、Maria Rangel

  DOI：10.1016/j.tet.2010.08.065

  日期：2010.10

  Two novel 3-hydroxy-4-pyridinone/naphthalene conjugates (L1 and L2) with different distances between the chelating and the fluorescent moieties were synthesized using conventional heating and microwave irradiation achieving a shorter reaction time. The structure of both compounds was confirmed by X-ray crystallography, revealing that these compounds were isolated as hydrochloride salts in dihydroxypyridinium forms. In solution and in the presence of a base, the tautomeric keto forms may be obtained as it was elucidated by NMR analysis. The dihydroxypyridinium form of L1 exhibits fluorescence at 450 nm, both in ACN and DMSO, whereas the corresponding keto form exhibits fluorescence at 365 nm. In contrast, the dihydroxypyridinium form of L2 only fluoresces in DMSO, exhibiting a band at 340 nm, while the keto form is non-fluorescent. These distinct fluorescent behaviors reveal that the tautomeric form in which the ligands are isolated and the distance between the chelating and fluorescent functions strongly influences their fluorescence properties. Ligand L1 exhibits better fluorescence properties and its fluorescence intensity is quenched in the presence of variable concentration of Cu2+, Zn2+, and Fe3+, thus making it suitable to be used as ion sensor. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, Modification, and Biological Evaluation of a Library of Novel Water‐Soluble Thiopyridone‐Based Organometallic Complexes and Their Unexpected (Biological) Behavior
  作者：Sophia Harringer、Barbara Happl、Marius Ozenil、Caroline Kast、Michaela Hejl、Debora Wernitznig、Anton A. Legin、Andreas Schweikert、Natalie Gajic、Alexander Roller、Gunda Koellensperger、Michael A. Jakupec、Wolfgang Kandioller、Bernhard K. Keppler

  DOI：10.1002/chem.201905546

  日期：2020.4.24

  A series of 16 dinuclear thiopyridone-based organometallics with excellent water solubility, increased stability and remarkable cytotoxicity were synthesized and characterized. The complexes of this work formed dimeric species featuring a double positive charge in polar protic solvents, accounting for their outstanding solubility in aqueous solution. Most of them displayed higher antiproliferative

  合成和表征了一系列16种具有优异水溶性，增加的稳定性和显着的细胞毒性的双核硫代吡啶酮基有机金属。这项工作的配合物形成了二聚体，在极性质子溶剂中具有双正电荷，这说明它们在水溶液中的出色溶解性。它们中的大多数显示出比其亲本硫代麦芽酚复合物更高的抗增殖活性，取决于所采用的金属中心，配体修饰和细胞系，其具有出乎意料的细胞毒性趋势。通过氨基酸相互作用研究，3D球体模型中的细胞毒性测试，激光消融，细胞蓄积测量以及细胞周期实验，收集了它们在生物系统中行为的见解。