6-phosphonopyrid-2-ylcarboxylic acid | 145432-83-3

• 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: 6-phosphonopyrid-2-ylcarboxylic acid
• 英文别名: pyridine-6-phospho-2-carboxylic acid；6-dihydroxyphosphorylpicolinic acid；6-carboxy-2-phosphonopyridine；6-phosphonopicolinic acid；H3dhppa；6-Phosphono-pyridine-2-carboxylic acid；6-phosphonopyridine-2-carboxylic acid
• CAS: 145432-83-3
• 化学式: C₆H₆NO₅P
• 分子量: 203.091
• InChiKey: QPYZTIAEXVIWNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二正丁基氧化锡 、 6-phosphonopyrid-2-ylcarboxylic acid 以 丙醇 、 苯 为溶剂， 以84%的产率得到di-n-butyltin pyridine-2-phosphonate-6-carboxylate dimer
  参考文献：
  名称：

  Synthesis and Structure of Di-n-Butyltin Pyridine-2-phosphonate-6-carboxylate

  摘要：

  The crystal structure of di-n-butyltin pyridine-2-phosphonate-6-carboxylate, [C14H24NO6PSn](2), features centrosymmetric dimers disposed about a central Sn2O2 core. The phosphonate carboxylate dianion is mu(2)-tetradentate, coordinating one tin atom via one of the phosphonate oxygen atoms, the pyridine nitrogen atom, and one of the carboxylate oxygen atoms; the latter atom also coordinates the second tin atom of the dimer. The remaining positions in the seven-coordinate, distorted pentagonal bipyramidal geometry are occupied by a water molecule and two n-butyl groups that occupy axial positions. The lattice is stabilized by hydrogen-bonding contacts leading to an arrangement of parallel, orthogonally related chains of dimeric units. In methanol solution, the dimer is involved in a dissociation equilibrium that is fast on the NMR time scale.

  DOI：

  10.1021/om9803725
• 作为产物：
  描述：

  6-溴-2-吡啶甲酸甲酯 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 6-phosphonopyrid-2-ylcarboxylic acid
  参考文献：
  名称：

  Dipicolinic acid异构体对金属β-内酰胺酶抑制作用的研究。

  摘要：

  新德里金属β-内酰胺酶-1（NDM-1）对我们最有效和处方最广泛的药物（含β-内酰胺类抗生素）构成了直接威胁。尽管已为NDM-1的开发做出了巨大努力，但尚无与临床相关的抑制剂可对抗NDM-1。使用羧酸基序结合Zn II的抑制剂在迄今为止报道的> 500种抑制剂中，NDM-1活性位点中的离子占很大一部分。迫切需要用于抑制剂开发的新的且结构多样的支架。本文中，我们报道了一个吡啶二甲酸（DPA）的羧酸基团的等位取代，以获得对NDM-1（以及相关的金属-β-内酰胺酶，IMP-1和VIM-2）具有良好抑制活性的DPA异构体。已确定，选择羧酸酯等排异构体会影响NDM-1抑制的效力和作用机理。此外，我们表明具有金属剥离机理的等排物可以重新设计成有利于三元络合物形成的抑制剂。这项工作为将来等规替代常规使用的金属结合基序提供了路线图（即，

  DOI：

  10.1002/cmdc.201900172

文献信息

• Structural Analogues of Selfotel
  作者：Zofia A. Dziuganowska、Katarzyna Ślepokura、Jean-Noël Volle、David Virieux、Jean-Luc Pirat、Paweł Kafarski

  DOI：10.1021/acs.joc.6b00220

  日期：2016.6.17

  A small library of phosphonopiperidylcarboxylic acids, analogues of NMDA antagonist selfotel (CGS 19755), was synthesized. First, the series of aromatic esters was obtained via a palladium-catalyzed cross-coupling reaction (Hirao coupling) of dialkyl phosphites with bromopyridinecarboxylates, followed by their hydrolysis. Then, hydrogenation of the resulting phosphonopyridylcarboxylic acids over PtO2

  合成了一个小的膦酰基哌啶基羧酸文库，它是NMDA拮抗剂selfotel（CGS 19755）的类似物。首先，通过亚磷酸二烷基酯与溴吡啶羧酸盐的钯催化的交叉偶联反应（Hirao偶联）获得一系列芳族酯。然后，将所得的膦酰基吡啶基羧酸在PtO 2上氢化，得到所需的膦酰基哌啶基羧酸。NMR研究表明氢化反应主要通过顺式加成进行。获得了几种化合物作为单晶结构。对神经元培养物进行的初步生物学研究表明，所获得的化合物具有针对NMDA受体的有希望的活性。
• Syntheses and Fe(II)/Fe(III) equilibria of the new multidentate ligands pyridine-2-phosphonic- 6-carbo×ylic acid and 2,6-pyridinediphosphonic acid for the use of their iron chelates as catalysts for the o×idation of H<sub>2</sub>S to S<sub>8</sub> by air
  作者：Dian Chen、Arthur E. Martell、Ramunas J. Motekaitis、Derek McManus

  DOI：10.1139/cjc-76-4-445

  日期：——

  The syntheses of two terdentate chelating agents, pyridine-2-phosphonic-6-carboxylic acid (2PP6C) and 2,6-pyridinediphosphonic acid (2,6PDPA), are described. The stepwise stability constants for the ferric complexes at 25.0 degrees C and mu=,0.100 M (KNO3) are log K-ML = 15.97 and log K-ML2 = 9.50 for 2PP6C, and log K-ML = 20.87 and log K(ML)2 = 7.81 for 2,6PDPA. Under the same conditions the stepwise formation constants for the ferrous chelates are log K-ML = 8.70 and log K-ML2 = 5.10 for 2PP6C, and log K-ML = 10.12 and log K-ML2 = 5.33 for 2,6PDPA. The stabilities of the Fe(III) and Fe(II) chelates are high enough to prevent precipitation of Fe(OH)(3) and FeS, respectively, from solutions having pH as high as 10.0. The rates of oxidative degradation of these ligands are very slow when the iron chelates are used as redox catalysts for the oxidation of H2S to S-8 by air. The rates of oxidative degradation are immeasurably slow when the iron chelates are used with sodium thiosulfate as a radical scavenger.
• Pyridine-2-phospho-carboxylic Acids: Synthesis and Properties
  作者：Bogdan Boduszek

  DOI：10.1002/prac.19923340515

  日期：——
• 6-Phosphoryl Picolinic Acids as Europium and Terbium Sensitizers
  作者：Julien Andres、Anne-Sophie Chauvin

  DOI：10.1021/ic200983y

  日期：2011.10.17

  Three 6-phosphoryl picolinic acid (6PPA) derivatives were synthesized and used as europium and terbium sensitizers. Two of the three ligands (6-diethoxyphosphoryl picolinic acid (Hdeppa) and 6-monoethoxyphosphoryl picofinic acid (H(2)meppa)) are water-soluble, once complexed to lanthanide ions, while the third (6-dihydroxyphosphoryl picolinic acid (H(3)dhppa)) forms a precipitate. The stability constants of the phosphoryl-based complexes were found to be higher than the carboxylate analogue (dipicolinic acid, H(2)dpa). The main species are the [LnL(3)] complexes under strict stoichiometric conditions, confirmed by (31)P NMR spectroscopy, mass spectrometry and lifetime analyses. The photophysical measurements reveal that the emission intensity of [Eu(deppa)(3)] is maximal at pH 4.8, whereas for [Eu(meppa)(3)](3-), the optimum pH is observed at 9.0. The lifetimes are all in the millisecond range and have confirmed the absence of water molecules in the first coordination sphere. The emissions of the terbium are always brighter than the corresponding europium within this phosphoryl series. The quantum yields of the phosphoryl containing complexes are lower than the carboxylate analogue ([Ln(dpa)(3)](3-)), except for [Tb(deppa)(3)], which exhibits an interesting quantum yield of 40% in aqueous solution.
• Synthesis and Structure of Di-<i>n</i>-Butyltin Pyridine-2-phosphonate-6-carboxylate
  作者：Marcel Gielen、Hassan Dalil、Laurent Ghys、Bogdan Boduszek、Edward R. T. Tiekink、José C. Martins、Monique Biesemans、Rudolph Willem

  DOI：10.1021/om9803725

  日期：1998.9.1

  The crystal structure of di-n-butyltin pyridine-2-phosphonate-6-carboxylate, [C14H24NO6PSn](2), features centrosymmetric dimers disposed about a central Sn2O2 core. The phosphonate carboxylate dianion is mu(2)-tetradentate, coordinating one tin atom via one of the phosphonate oxygen atoms, the pyridine nitrogen atom, and one of the carboxylate oxygen atoms; the latter atom also coordinates the second tin atom of the dimer. The remaining positions in the seven-coordinate, distorted pentagonal bipyramidal geometry are occupied by a water molecule and two n-butyl groups that occupy axial positions. The lattice is stabilized by hydrogen-bonding contacts leading to an arrangement of parallel, orthogonally related chains of dimeric units. In methanol solution, the dimer is involved in a dissociation equilibrium that is fast on the NMR time scale.