3-(benzyloxy)-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid | 593247-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(benzyloxy)-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
• 英文别名: 3-benzyloxy-4-carboxy-6-methyl-2(1H)-pyridinone；6-methyl-2-oxo-3-phenylmethoxy-1H-pyridine-4-carboxylic acid
• CAS: 593247-65-5
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: CNNXHBVSLMLOQP-UHFFFAOYSA-N

物化性质

• 沸点：
  498.6±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid 在 盐酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 水 为溶剂， 以95%的产率得到3-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
  参考文献：
  名称：

  Structure–Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease

  摘要：

  Metalloenzymes represent an important target space for drug discovery. A limitation to the early development of metalloenzyme inhibitors has been the lack of established structure-activity relationships (SARs) for molecules that bind the metal ion cofactor(s) of a metalloenzyme. Herein, we employed a bioinorganic perspective to develop an SAR for inhibition of the metalloenzyme influenza RNA polymerase PA(N) endonuclease. The identified trends highlight the importance of the electronics of the metal-binding pharmacophore (MBP), in addition to MBP sterics, for achieving improved inhibition and selectivity. By optimization of the MBPs for PA(N) endonuclease, a class of highly active and selective fragments was developed that displays IC50 values <50 nM. This SAR led to structurally distinct molecules that also displayed IC50 values of similar to 10 nM, illustrating the utility of a metal-centric development campaign in generating highly active and selective metalloenzyme inhibitors.

  DOI：

  10.1021/acs.jmedchem.8b01363
• 作为产物：
  描述：

  ethyl 3-hydroxy-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate 在 氯化十六烷基吡啶 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 3-(benzyloxy)-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid
  参考文献：
  名称：

  一种双3，2-羟基吡啶酮类衍生物及其制备方 法和用途

  摘要：

  本发明公开了一种双3，2‑羟基吡啶酮类衍生物及其制备方法和用途，其特点是所述双3，2‑羟基吡啶酮类衍生物以氯丙酮、丁二酸酮钠盐衍生物和氨气在Lewis酸催化下发生迈克尔加成和酰胺化反应构建2，3‑羟基吡啶酮类片段，该片段经过苄基保护后通过强碱性条件下的皂化反应水解乙酯得到4位羧酸，然后使用赖氨酸与活化的3，2‑羟基吡啶酮类衍生物发生酰胺化反应得到苄基保护的目标产物前体，最后通过Pd/C在H2条件下脱除苄基得到目标双3，2‑羟基吡啶酮类衍生物。本发明的化合物的结构特点是，双羟基吡啶酮具有独特的齿状结构，赖氨酸基团的引入使得可与金属离子形成稳定的配合物，从而可作为一种潜在的促排剂应用于生物体内金属促排等领域。

  公开号：

  CN106748995B

文献信息

• 一种双3，2-羟基吡啶酮类衍生物及其制备方 法和用途
  申请人：中国工程物理研究院核物理与化学研究所

  公开号：CN106748995B

  公开（公告）日：2019-06-18

  本发明公开了一种双3，2‑羟基吡啶酮类衍生物及其制备方法和用途，其特点是所述双3，2‑羟基吡啶酮类衍生物以氯丙酮、丁二酸酮钠盐衍生物和氨气在Lewis酸催化下发生迈克尔加成和酰胺化反应构建2，3‑羟基吡啶酮类片段，该片段经过苄基保护后通过强碱性条件下的皂化反应水解乙酯得到4位羧酸，然后使用赖氨酸与活化的3，2‑羟基吡啶酮类衍生物发生酰胺化反应得到苄基保护的目标产物前体，最后通过Pd/C在H2条件下脱除苄基得到目标双3，2‑羟基吡啶酮类衍生物。本发明的化合物的结构特点是，双羟基吡啶酮具有独特的齿状结构，赖氨酸基团的引入使得可与金属离子形成稳定的配合物，从而可作为一种潜在的促排剂应用于生物体内金属促排等领域。
• Hydroxypyridonate and hydroxypyrimidinone chelating agents
  申请人：Raymond N. Kenneth

  公开号：US20050008570A1

  公开（公告）日：2005-01-13

  The present invention provides hydroxypyridinone and hydroxypyrimidone chelating agents. Also provides are Gd(III) complexes of these agents, which are useful as contrast enhancing agents for magnetic resonance imaging. The invention also provides methods of preparing the compounds of the invention, as well as methods of using the compounds in magnetic resonance imaging applications.

  本发明提供了羟基吡啶酮和羟基嘧啶酮螯合剂。还提供了这些剂的Gd(III)配合物，这些配合物可用作磁共振成像的造影增强剂。该发明还提供了制备本发明化合物的方法，以及在磁共振成像应用中使用这些化合物的方法。
• [EN] MACROCYCLIC HOPO CHELATORS<br/>[FR] CHÉLATEURS HOPO MACROCYCLIQUES
  申请人：LUMIPHORE INC

  公开号：WO2011025790A1

  公开（公告）日：2011-03-03

  The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability.

  本发明提供了一种新型的大环化合物类别，以及由金属离子（例如，镧系元素）与本发明的化合物形成的配合物。首选的配合物在水介质中表现出高稳定性，以及镧系离子的发光量子产率高，而无需辅助激活剂。首选的化合物包括其大环结构中的羟基吡啶酮基团，并以对多种多肽（如抗体和蛋白质）的非特异性结合惊人地低以及高动力学稳定性为特征。
• MACROCYCLIC HOPO CHELATORS
  申请人：Butlin Nathaniel G.

  公开号：US20120214253A1

  公开（公告）日：2012-08-23

  The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability.

  本发明提供了一类新型的大环化合物，以及由金属（例如镧系金属）离子和本发明中的化合物形成的络合物。优选的络合物在无需次级活化剂的情况下，具有高稳定性和高量子产率的镧系离子荧光。优选的化合物在它们的大环结构中包括羟基吡啶酮基团，并且其特点是与各种多肽（如抗体和蛋白质）具有惊人的低非特异性结合和高动力学稳定性。
• Hopo chelators
  申请人：Lumiphore, Inc.

  公开号：EP2816038A1

  公开（公告）日：2014-12-24

  The present invention provides a novel class of macrocyclic compounds of formula (I) as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability. (I)

  本发明提供了一类新型的式(I)大环化合物以及金属（如镧系元素）离子与本发明化合物之间形成的配合物。优选的配合物在水介质中表现出高稳定性和高镧系离子发光量子产率，无需二次活化剂。优选化合物在其大环结构中包含羟基吡啶壬基，其特点是与抗体和蛋白质等多种多肽的非特异性结合率低得出奇，并且具有很高的动力学稳定性。 (I)