2-aminomethyl-5-benzyloxy-pyran-4-one | 60923-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-aminomethyl-5-benzyloxy-pyran-4-one
• 英文别名: 2-(aminomethyl)-5-(benzyloxy)-4H-pyran-4-one；2-(aminomethyl)-5-phenylmethoxypyran-4-one
• CAS: 60923-15-1
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: CNWWNLNRJOUVKM-UHFFFAOYSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  449.7±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-aminomethyl-5-benzyloxy-pyran-4-one 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(5-hydroxy-4-oxopyran-2-yl)methyl]-2-(7-methoxy-2-oxochromen-4-yl)acetamide
  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
• 作为产物：
  描述：

  曲酸 在 氯化亚砜 、 sodium azide 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-aminomethyl-5-benzyloxy-pyran-4-one
  参考文献：
  名称：

  基于片段的流感核酸内切酶抑制剂的鉴定

  摘要：

  流感病毒每年造成数百万例严重疾病。疫苗效力的逐年变化，加上新出现的耐药性，有必要开发用于治疗流感感染的新药。一种有吸引力的靶标是RNA依赖性RNA聚合酶PA亚基。本文中，我们报道了从金属结合药效团（MBP）库筛选中鉴定出的先导化合物衍生的流感PA核酸内切酶抑制剂的发展。发现焦果烯酸及其衍生物是核酸内切酶的有效抑制剂。在建模和先前报道的结构数据的指导下，从MBP命中中精心制作了分子的几个子库。建立了结构与活动的关系，使用片段增长和片段合并策略设计和合成了更有效的分子。这种方法最终导致了带有IC的铅化合物的开发50值为14 nM，显示MDCK细胞中针对H1N1流感病毒的EC 50值为2.1μM。

  DOI：

  10.1021/acs.jmedchem.6b00628

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING INFLUENZA RNA POLYMERASE PA ENDONUCLEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR INHIBER L'ENDONUCLÉASE DE LA PA DE L'ARN POLYMÉRASE DE LA GRIPPE
  申请人：UNIV CALIFORNIA

  公开号：WO2017156194A1

  公开（公告）日：2017-09-14

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  其中提供了金属酶抑制剂，例如流感A病毒RNA依赖性RNA聚合酶PA亚基内切酶的抑制剂，以及其合成和使用方法。
• PYRIDONE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELORIATION OR PREVENTION OF A VIRAL DISEASE
  申请人：Savira pharmaceuticals GmbH

  公开号：US20140194476A1

  公开（公告）日：2014-07-10

  The present invention relates to a compound having the general formula (II), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

  本发明涉及具有通式（II）的化合物，可选地以药学上可接受的盐、溶剂合物、多形体、伴药、共晶、前药、互变异构体、外消旋体、对映体或二对映体或其混合物的形式存在，这些化合物在治疗、缓解或预防病毒性疾病方面是有用的。此外，还披露了具体的联合疗法。
• Pyridone derivatives and their use in the treatment, ameloriation or prevention of a viral disease
  申请人：Savira pharmaceuticals GmbH

  公开号：US08952039B2

  公开（公告）日：2015-02-10

  The present invention relates to a compound having the general formula (II), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

  本发明涉及一种具有一般式（II）的化合物，可选地以药学上可接受的盐、溶剂合物、多晶形、共药、共晶体、前药、互变异构体、外消旋体、对映体或其混合物的形式存在，这些化合物对治疗、缓解或预防病毒性疾病有用。此外，还揭示了特定的联合治疗方法。
• Pyrone based compounds for treating bacterial infections
  申请人：FORGE THERAPEUTICS, INC.

  公开号：US10611747B2

  公开（公告）日：2020-04-07

  The present teachings relate to pyrone derivatives, pharmaceutical compositions thereof, and methods of using such compounds to treat bacterial infections.

  本教导涉及吡喃酮衍生物、其药物组合物以及使用此类化合物治疗细菌感染的方法。
• Compositions and methods for inhibiting influenza RNA polymerase PA endonuclease
  申请人：The Regents of the University of California

  公开号：US10889556B2

  公开（公告）日：2021-01-12

  There are provided inter alia metalloenzyme inhibitors, such as inhibitors of influenza A RNA dependent RNA polymerase PA subunit endonuclease, and methods of synthesis and use of the same.

  除其他外，还提供了金属酶抑制剂，例如甲型流感 RNA 依赖性 RNA 聚合酶 PA 亚基内切酶抑制剂，以及合成和使用这些抑制剂的方法。