N-(3,4-dihydroxyphenethyl)picolinamide

• 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: N-(3,4-dihydroxyphenethyl)picolinamide
• 英文别名: N-[2-(3,4-dihydroxyphenyl)ethyl]pyridine-2-carboxamide
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: SFBXFKCFJZZXKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  82.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 N-(3,4-dihydroxyphenethyl)picolinamide 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以63%的产率得到[chloride{N-(3,4-dihydroxyphenethyl)picolinamide}(η⁶-p-cymene)ruthenium(II)]chloride
  参考文献：
  名称：

  Design of organoruthenium complexes for nanoparticle functionalization

  摘要：

  In recent years, extensive research efforts have been focused on loading metal complexes onto macromolecular systems such as nanoparticles. We report a ligand with a catechol group based on a picolinamide which allows for coordination to organoruthenium moieties while the catechol group remains available for loading on nanoparticles as delivery vehicles towards tumors. All the compounds were characterized with standard analytical methods and the molecular structure of the ligand 1, and its Ru complexes 1a and 1b were determined by X-ray diffraction analysis. The crystal structure of 1a and 1b showed pseudo-tetrahedral geometry of the Ru center with "piano-stool" conformation and 1 coordinated as an N, O-bidentate ligand, however, the latter depending on the reaction conditions employed. The Ru complexes 1a-1c were effectively loaded on magnetite nanoparticles as characterized by inductively-coupled plasma mass spectrometry (ICP-MS), transmission electron microscopy (TEM) and Fourier transform infrared spectroscopy (FTIR). (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2019.03.020
• 作为产物：
  描述：

  2-吡啶甲酸 、 盐酸多巴胺 在 sodium methylate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以37%的产率得到N-(3,4-dihydroxyphenethyl)picolinamide
  参考文献：
  名称：

  Design of organoruthenium complexes for nanoparticle functionalization

  摘要：

  In recent years, extensive research efforts have been focused on loading metal complexes onto macromolecular systems such as nanoparticles. We report a ligand with a catechol group based on a picolinamide which allows for coordination to organoruthenium moieties while the catechol group remains available for loading on nanoparticles as delivery vehicles towards tumors. All the compounds were characterized with standard analytical methods and the molecular structure of the ligand 1, and its Ru complexes 1a and 1b were determined by X-ray diffraction analysis. The crystal structure of 1a and 1b showed pseudo-tetrahedral geometry of the Ru center with "piano-stool" conformation and 1 coordinated as an N, O-bidentate ligand, however, the latter depending on the reaction conditions employed. The Ru complexes 1a-1c were effectively loaded on magnetite nanoparticles as characterized by inductively-coupled plasma mass spectrometry (ICP-MS), transmission electron microscopy (TEM) and Fourier transform infrared spectroscopy (FTIR). (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2019.03.020

文献信息

• 10.1021/acs.joc.4c00988
  作者：Bag, Raghunath、Sharma, Nagendra K.

  DOI：10.1021/acs.joc.4c00988

  日期：——

  a Pd-catalyzed picolinamide-directed site-selective C(sp2)–H sulfonylation of amino acids and peptides with sodium sulfinates in moderate to good yields. Sulfonylation of levodopa and dopamine drug molecules and late-stage directed peptide sulfonylation are studied for the first time. Broad substrate scope having various functionalities, late-stage drug modifications, and various post synthetic utilities

  本报告描述了 Pd 催化的吡啶甲酰胺定向位点选择性 C（sp2）-H 氨基酸和肽与亚磺酸钠的磺酰化反应，产率中等至良好。首次研究了左旋多巴和多巴胺药物分子的磺酰化以及晚期定向肽磺酰化。潜在的优势包括具有各种功能的广泛底物范围、后期药物修饰以及各种合成后实用程序，如硫属化、溴化、烯化和芳基化。
• Design of organoruthenium complexes for nanoparticle functionalization
  作者：Saawan Kumar、Guillaume Gallician、Dennis Weidener、Matthew P. Sullivan、Tilo Söhnel、Muhammad Hanif、Christian G. Hartinger

  DOI：10.1016/j.jorganchem.2019.03.020

  日期：2019.8

  In recent years, extensive research efforts have been focused on loading metal complexes onto macromolecular systems such as nanoparticles. We report a ligand with a catechol group based on a picolinamide which allows for coordination to organoruthenium moieties while the catechol group remains available for loading on nanoparticles as delivery vehicles towards tumors. All the compounds were characterized with standard analytical methods and the molecular structure of the ligand 1, and its Ru complexes 1a and 1b were determined by X-ray diffraction analysis. The crystal structure of 1a and 1b showed pseudo-tetrahedral geometry of the Ru center with "piano-stool" conformation and 1 coordinated as an N, O-bidentate ligand, however, the latter depending on the reaction conditions employed. The Ru complexes 1a-1c were effectively loaded on magnetite nanoparticles as characterized by inductively-coupled plasma mass spectrometry (ICP-MS), transmission electron microscopy (TEM) and Fourier transform infrared spectroscopy (FTIR). (C) 2019 Elsevier B.V. All rights reserved.