6-(carboxymethyl)-pyridine-2-carboxylic acid | 1451194-10-7

• 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-(carboxymethyl)-pyridine-2-carboxylic acid
• 英文别名: 6-(carboxymethyl)picolinic acid；6-(Carboxymethyl)pyridine-2-carboxylic acid；6-(carboxymethyl)pyridine-2-carboxylic acid
• CAS: 1451194-10-7
• 化学式: C₈H₇NO₄
• 分子量: 181.148
• InChiKey: OKLYHFLTMGKYNL-UHFFFAOYSA-N

物化性质

• 沸点：
  435.4±35.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(carboxymethyl)-pyridine-2-carboxylic acid 、 [Pd(CH2-8-quinolyl)(OAc)]2 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以99%的产率得到
  参考文献：
  名称：

  Aerobic C–H Acetoxylation of 8-Methylquinoline in Pd^II–Pyridinecarboxylic Acid Systems: Some Structure–Reactivity Relationships

  摘要：

  Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O-2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O-2 activation steps shows that the C-H activation step is rate-limiting, whereas the O-2 activation occurs at a much faster rate already at 20 degrees C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.

  DOI：

  10.1021/om400618n
• 作为产物：
  描述：

  乙基 6-甲基吡啶-2-羧酸酯 以 四氢呋喃 、 水 为溶剂， 反应 78.0h， 生成 6-(carboxymethyl)-pyridine-2-carboxylic acid
  参考文献：
  名称：

  Aerobic C–H Acetoxylation of 8-Methylquinoline in Pd^II–Pyridinecarboxylic Acid Systems: Some Structure–Reactivity Relationships

  摘要：

  Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O-2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O-2 activation steps shows that the C-H activation step is rate-limiting, whereas the O-2 activation occurs at a much faster rate already at 20 degrees C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.

  DOI：

  10.1021/om400618n

文献信息

• Investigation of Dipicolinic Acid Isosteres for the Inhibition of Metallo‐β‐Lactamases
  作者：Allie Y. Chen、Pei W. Thomas、Zishuo Cheng、Nasa Y. Xu、David L. Tierney、Michael W. Crowder、Walter Fast、Seth M. Cohen

  DOI：10.1002/cmdc.201900172

  日期：2019.7.3

  one carboxylate group of dipicolinic acid (DPA) to obtain DPA isosteres with good inhibitory activity against NDM‐1 (and related metallo‐β‐lactamases, IMP‐1 and VIM‐2). It was determined that the choice of carboxylate isostere influences both the potency of NDM‐1 inhibition and the mechanism of action. Additionally, we show that an isostere with a metal‐stripping mechanism can be re‐engineered into an

  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，