1-羟基-6-氧代-1,6-二氢吡啶-2-羧酸 | 94781-89-2

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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
• 中文名称: 1-羟基-6-氧代-1,6-二氢吡啶-2-羧酸
• 英文名称: 1-hydroxy-6-oxo-1,6-dihydropyridine-2-carboxylic acid
• 英文别名: 6-carboxy-1-hydroxy-2(1H)-pyridinone；1-(hydroxy)-2-pyridinone-6-carboxylic acid；1-hydroxy-6-oxopyridine-2-carboxylic acid
• CAS: 94781-89-2
• 化学式: C₆H₅NO₄
• mdl: MFCD20270107
• 分子量: 155.11
• InChiKey: QJEZBSWVHDOAFS-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  365.1±52.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-羟基-6-氧代-1,6-二氢吡啶-2-羧酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 1-hydroxy-6-oxo-1,6-dihydropyridine-2-carbonyl chloride
  参考文献：
  名称：

  Evaluation of DFO-HOPO as an octadentate chelator for zirconium-89

  摘要：

  基于⁸⁹Zr的免疫PET的未来取决于开发具有比目前使用的去铁胺（DFO）更好稳定性的新螯合剂。

  DOI：

  10.1039/c7cc03572a
• 作为产物：
  描述：

  1,6-dihydroxypicolinic acid 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以95%的产率得到1-羟基-6-氧代-1,6-二氢吡啶-2-羧酸
  参考文献：
  名称：

  Synthesis of chromium(III) complex with 1-hydroxy-2-pyridinone-6-carboxylic acid as insulin-mimetic agent and its spectroscopic and computational studies

  摘要：

  The new complex of chromium(III) and 1-hydroxy-2-pyridinone-6-carboxylic acid was synthesized and its preparation routes were reported. Mass spectrometry and elemental analysis indicated the formation of chromium complex with the metal-to-ligand mole ratio of 1:3. Combination of spectroscopic measurement and spectral computations based on the density functional theory suggested that 1-hydroxy-2-pyridinone-6-carboxylic acid was a bidentate ligand using one oxygen atom at pyridinone carbonyl group and the other at N-oxide group as donor atoms upon chelation with chromium(III), forming the six-coordinate complex with five-membered chelate rings. Due to the enhanced stability of the chelate rings, such the pathway of chelation was theoretically predicted to be more favorable than the case where the carboxylate oxygen atom of ligand participated in the chelation. According to the preliminary tests, the chromium(III) complex with 1-hydroxy-2-pyridinone-6-carboxylic acid was found to be active in lowering plasma glucose levels in vivo. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.07.041

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。
• [EN] IRON(III) AND GALLIUM(III) METAL ORGANIC POLYHEDRA, METHODS OF MAKING SAME, AND USES THEREOF<br/>[FR] POLYÈDRES ORGANIQUES MÉTALLIQUES DE FER(III) ET DE GALLIUM(III), LEURS PROCÉDÉS DE FABRICATION ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2020263761A1

  公开（公告）日：2020-12-30

  Compounds may have at least two structural units, which may be referred to as ligands. Each structural unit includes at least one spacer group and two or more donor groups. Compounds may have two or more iron(III) cations, one or more of which may be a high- spin iron(III) cation or high-spin iron(III) cations, two or more gallium(III) cations, or at least one iron(III) cation, one or more of which may be a high-spin iron(III) cation or high-spin iron(III) cations, and at least one gallium(III) cation, where the iron(III) cation(s) and/or the gallium(III) cation(s) coordinate to the donor groups. The compounds may be self-assembled cages. A composition may include one or more of the compound(s) and a pharmaceutically accepted carrier. Methods of imaging use one or more of the compound(s) and/or one or more of the composition(s).

  化合物可能至少有两个结构单元，可以称为配体。每个结构单元包括至少一个间隔基团和两个或更多供体基团。化合物可能具有两个或更多个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，两个或更多个镓（III）阳离子，或至少一个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，和至少一个镓（III）阳离子，其中铁（III）阳离子和/或镓（III）阳离子与供体基团配位。这些化合物可能是自组装笼状结构。一种组合物可能包括一个或多个这些化合物和一个药用可接受的载体。成像方法使用一个或多个这些化合物和/或一个或多个这些组合物。
• Synthesis and iron chelating properties of hydroxypyridinone and hydroxypyranone hexadentate ligands
  作者：Tao Zhou、Xiao-Le Kong、Robert C Hider

  DOI：10.1039/c8dt05014g

  日期：——

  chelators, four hexadentate ligands were synthesized by conjugating the corresponding bidentate ligands (3-hydroxypyridin-4-one (3,4-HOPO), 3-hydroxypyridin-2-one (3,2-HOPO), 1-hydroxypyridin-2-one (1,2-HOPO), and 3-hydroxypyran-4-one) each with a free amino group to a tripodal acid. Their pKa values and affinities for iron(III) were investigated. The pFe3+ values of the hexadentate pyridinones 1 (3

  螯合疗法已成为治疗某些疾病的重要方法。为了确定临床上有用的螯合剂，通过缀合相应的二齿配体（3-羟基吡啶-4-酮（3,4-HOPO），3-羟基吡啶-2-酮（3,2-HOPO）， 1-羟基吡啶-2-酮（1,2-HOPO）和3-羟基吡喃-4-酮）各自具有与三脚架酸形成的游离氨基。研究了它们对铁（III）的p K a值和亲和力。该PFE 3+的六齿吡啶酮的值1（3,4- HOPO），3（3,2-HOPO）和4（1,2- HOPO）和吡喃酮2被发现跟随序列1 >4 » 3 > 2，这是对PFE不同3+的相应的二齿形式（3,4- HOPO»3,2-HOPO> 1,2- HOPO> 3- hydroxypyranone）值序列。六齿的3,4-HOPO和1,2-HOPO具有最大的除铁剂潜力。
• Synthesis of novel Iron(III) chelators based on triaza macrocycle backbone and 1-hydroxy-2(H)-pyridin-2-one coordinating groups and their evaluation as antimicrobial agents
  作者：David G. Workman、Michael Hunter、Lynn G. Dover、David Tétard

  DOI：10.1016/j.jinorgbio.2016.04.018

  日期：2016.7

  Several novel chelators based on 1-hydroxy-2(1H)-pyridinone coordinating groups decorating a triaza macrocyclic backbone scaffold were synthesised as potential powerful Fe(3+) chelators capable of competing with bacterial siderophores. In particular, a novel chloromethyl derivative of 1-hydroxy-2(1H)-pyridinone exploiting a novel protective group for this family of coordinating groups was developed

  几个新颖的螯合剂基于1-羟基-2（1H）-吡啶酮配位基团装饰Triaza大环骨架骨架作为潜在的强大Fe（3+）螯合剂能够与细菌铁载体竞争。特别地，开发了一种新的1-羟基-2（1H）-吡啶酮的氯甲基衍生物，其为该配位基团家族开发了新的保护基。这些是基于1-羟基-2（1H）-吡啶酮的六齿螯合剂的第一个例子，被证明对一系列病原菌具有生物活性。评估了它们作为生物抑制剂的功效，揭示了螯合剂结构的微小变化会深刻影响功效。我们经过最佳测试的新型螯合剂的最低抑菌浓度接近于或等于1,4，7-三（3-羟基-6-甲基-2-吡啶甲基）-1,4,7-三氮杂环壬烷，迄今为止已知的最佳Fe（3+）螯合剂。这些螯合剂对微生物生长的阻滞作用表明，它们可以作为抗菌素与抗生素一起作为潜在的抗感染药物。
• Synthesis and Initial Evaluation for In Vivo Chelation of Pu(IV) of a Mixed Octadentate Spermine-Based Ligand Containing 4-Carbamoyl-3-hydroxy-1-methyl-2(1<i>H</i>)-pyridinone and 6-Carbamoyl-1-hydroxy-2(1<i>H</i>)-pyridinone
  作者：Jide Xu、Patricia W. Durbin、Birgitta Kullgren、Shirley N. Ebbe、Linda C. Uhlir、Kenneth N. Raymond

  DOI：10.1021/jm010564t

  日期：2002.8.1

  An improved synthesis for a series of 1-hydroxy-2(1H)-pyridinone-based octadentate ligands is reported. The mixed chelate, octadentate ligand, 3,4,3-LI(1,2-Me-3,2-HOPO), was designed, synthesized, and tested for in vivo chelation of Pu in a mouse model. This ligand incorporates both 1,2-HOPO and Me-3,2-HOPO metal chelating units; the latter has higher affinity toward actinide ions than does 1,2-HOPO

  报道了一系列基于1-羟基-2（1H）-吡啶酮的八齿配体的合成方法的改进。设计，合成了混合的螯合物，八齿配体3,4,3-LI（1,2-Me-​​3,2-HOPO），并在小鼠模型中测试了Pu的体内螯合。该配体结合了1,2-HOPO和Me-3,2-HOPO金属螯合单元。在生理pH下，后者对act系离子的亲和力高于1,2-HOPO。以30 micromol / kg的标准临床剂量向禁食或正常喂养的小鼠口服或口服3,4,3-LI（1,2-HOPO）和3,4,3-LI（1,2-Me- 3,2-HOPO）除去注入的CaNa（3）DTPA明显更多的Pu。这些HOPO配体的0.1毫克/千克的注射剂量与30毫摩尔/千克的CaNa（3）DTPA注射一样有效。每天十次注射30 micromol / kg的HOPO配体未在小鼠中诱发可检测的急性毒性。口服时，混合的HOPO配体比3,4,3-LI（1,2-HOPO）更