2,6-bis((4-hydroxybenzene)carbamoyl)pyridine | 1154745-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-bis((4-hydroxybenzene)carbamoyl)pyridine
• 英文别名: N2,N6-bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide；bis(4-hydroxyphenyl)-2,6-pyridinedicarboxamide；2-N,6-N-bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide
• CAS: 1154745-22-8
• 化学式: C₁₉H₁₅N₃O₄
• 分子量: 349.346
• InChiKey: HBZFVCBBQKGBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-呋喃甲胺 、 2,6-bis((4-hydroxybenzene)carbamoyl)pyridine 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以17%的产率得到N2,N6-bis({3-[(furan-2-yl)methyl]-3,4-dihydro-2H-1,3-benzoxazin-6-yl})pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  How Does the Hydrogen Bonding Interaction Influence the Properties of Polybenzoxazine? An Experimental Study Combined with Computer Simulation

  摘要：

  The formation of intra- or intermolecular hydrogen bonding and their influences on polybenzoxazine's properties were investigated after the model benzoxazine monomers (o-AB-fbz, o-AF-fbz, o-AP-fbz, p-AB-fbz, p-AF-fbz, p-AP-fbz) were synthesized. Because of the different electron-donating abilities of bridging units (benzene, furan and pyridine) in isophthalic acid (IPA), 2,5-furandicarboxylic acid (2,5-FDCA) and 2,6-pyridinedicarboxylic acid (2,6-PDCA), the strength of intramolecular H-bonding involved with the oxygen atom in oxazine ring in o-AB-fbz, o-AF-fbz and o-AP-fbz followed the order of o-AB-fbz > o-AF-fbz > o-AP-fbz, and the strength of the overall H-bonding was arranged as follows: o-AB-fbz < o-AF-fbz < oAP-fbz. While more intermolecular H-bonding was formed in p-AB-fbz and p-AF-fbz as well as p-AP-fbz. DSC and FT-IR results discovered the relationship between the H-bonding involved with the oxygen atom in oxazine ring and the curing activities of benzoxazines. After curing reaction, the cured systems showed varied glass transition temperature (Tg), and the influence of H-bonding on Tg was revealed by in situ FT-IR analysis. Molecular dynamics (MD) simulation was also applied to investigate the properties of synthesized polybenzoxazines and similar results were obtained. Not only the formation of H-bonding but also their effects on both the curing behaviors of benzoxazine monomers and the thermal properties of cured resins were systematically investigated, which would help us understand polybenzoxazines more deeply and might be a guideline for improving their comprehensive properties only by manipulating the H-bonding.

  DOI：

  10.1021/acs.macromol.8b00741
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 氯化亚砜 、 N,N-二甲基乙酰胺 、 三甲胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2,6-bis((4-hydroxybenzene)carbamoyl)pyridine
  参考文献：
  名称：

  How Does the Hydrogen Bonding Interaction Influence the Properties of Polybenzoxazine? An Experimental Study Combined with Computer Simulation

  摘要：

  The formation of intra- or intermolecular hydrogen bonding and their influences on polybenzoxazine's properties were investigated after the model benzoxazine monomers (o-AB-fbz, o-AF-fbz, o-AP-fbz, p-AB-fbz, p-AF-fbz, p-AP-fbz) were synthesized. Because of the different electron-donating abilities of bridging units (benzene, furan and pyridine) in isophthalic acid (IPA), 2,5-furandicarboxylic acid (2,5-FDCA) and 2,6-pyridinedicarboxylic acid (2,6-PDCA), the strength of intramolecular H-bonding involved with the oxygen atom in oxazine ring in o-AB-fbz, o-AF-fbz and o-AP-fbz followed the order of o-AB-fbz > o-AF-fbz > o-AP-fbz, and the strength of the overall H-bonding was arranged as follows: o-AB-fbz < o-AF-fbz < oAP-fbz. While more intermolecular H-bonding was formed in p-AB-fbz and p-AF-fbz as well as p-AP-fbz. DSC and FT-IR results discovered the relationship between the H-bonding involved with the oxygen atom in oxazine ring and the curing activities of benzoxazines. After curing reaction, the cured systems showed varied glass transition temperature (Tg), and the influence of H-bonding on Tg was revealed by in situ FT-IR analysis. Molecular dynamics (MD) simulation was also applied to investigate the properties of synthesized polybenzoxazines and similar results were obtained. Not only the formation of H-bonding but also their effects on both the curing behaviors of benzoxazine monomers and the thermal properties of cured resins were systematically investigated, which would help us understand polybenzoxazines more deeply and might be a guideline for improving their comprehensive properties only by manipulating the H-bonding.

  DOI：

  10.1021/acs.macromol.8b00741

文献信息

• Syntheses, characterization, and anti-cancer activities of pyridine-amide based compounds containing appended phenol or catechol groups
  作者：AFSAR ALI、DEEPAK BANSAL、NAGENDRA K KAUSHIK、NEHA KAUSHIK、EUN HA CHOI、RAJEEV GUPTA

  DOI：10.1007/s12039-014-0671-3

  日期：2014.7

  Several pyridine-amide compounds appended with phenol/catechol groups are synthesized. These compounds consist of protected or deprotected phenol/catechol groups and offer pyridine, amide, and phenol/catechol functional groups. All compounds have been well-characterized by various spectroscopic methods, elemental analysis, thermal studies, and crystallography. The biological activities of all compounds were investigated while a few compounds significantly decreased the metabolic viability, growth and clonogenicity of T98G cells in dose dependent manner. Accumulation of ROS was observed in T98G cells, which displayed a compromised redox status as evident from increased cellular Caspase 3/7 activity and formation of micronuclei. The in silico pharmacokinetic studies suggest that all compounds have good bioavailability, water solubility and other drug-like parameters. A few compounds were identified as the lead molecules for future investigation due to their: (a) high activity against T98G brain, H-460 lung, and SNU-80 thyroid cancer cells; (b) low cytotoxicity in non-malignant HEK and MRC-5 cells; (c) low toxic risks based on in silico evaluation; (d) good theoretical oral bioavailability according to Lipinski ‘rule of five′ pharmacokinetic parameters; and (e) better drug-likeness and drug-score values.

  合成了几种带有酚/儿茶酚基团的吡啶酰胺化合物。这些化合物包括已保护或未保护的酚/儿茶酚基团，并提供了吡啶、酰胺和酚/儿茶酚官能团。所有化合物均已通过多种光谱方法、元素分析、热学研究和结晶学进行了充分的表征。所有化合物的生物活性均已得到研究，其中少数化合物在剂量依赖性方式下显著降低了T98G细胞的代谢活力、生长和克隆能力。在T98G细胞中观察到了ROS的积累，这些细胞显示出了受损的氧化还原状态，这一点从增加的细胞Caspase 3/7活性和微核的形成中可以明显看出。计算机模型药代动力学研究显示，所有化合物均具有良好的生物利用度、水溶性和其他类药物参数。由于以下原因，少数化合物被确定为未来研究的潜在先导分子：（a）对T98G脑、H-460肺和SNU-80甲状腺癌细胞具有高活性；（b）对非恶性HEK和MRC-5细胞具有低细胞毒性；（c）基于计算机模型的评估显示低毒性风险；（d）根据Lipinski的“五规则”药代动力学参数显示良好的理论口服生物利用度；以及（e）更好的药物相似性和药物评分值。
• Effect of metal coordination on the interaction of substituted phenanthroline and pyridine ligands with quadruplex DNA
  作者：Julie E. Reed、Andrew J. P. White、Stephen Neidle、Ramón Vilar

  DOI：10.1039/b820086f

  日期：——

  prepared and their coordination chemistry to platinum(II) and palladium(II) investigated. Both the ligands and metal complexes have been designed with the appropriate geometric requirements to favour pi-pi interactions with guanine quartets, which are the core motif in quadruplex structures formed by folding single-stranded telomeric DNA. The interactions of these compounds with quadruplex-DNA have

  制备了一系列新的单羧酰胺基菲咯啉和双羧酰胺基吡啶，并研究了它们与铂（II）和钯（II）的配位化学。配体和金属配合物的设计均具有适当的几何要求，以促进与鸟嘌呤四联体的pi-pi相互作用，这是折叠单链端粒DNA形成的四链体结构的核心基序。已经研究了这些化合物与四链体DNA的相互作用。结果表明，其中一些化合物可诱导四链体DNA的稳定化（例如，一种铂（II）络合物在20摄氏度下，在1 microM时的DeltaTm），而在相似浓度下与双链体DNA之间没有可测量的相互作用。此外，
• How Does the Hydrogen Bonding Interaction Influence the Properties of Polybenzoxazine? An Experimental Study Combined with Computer Simulation
  作者：Xiaobin Shen、Lijun Cao、Yuan Liu、Jinyue Dai、Xiaoqing Liu、Jin Zhu、Shiyu Du

  DOI：10.1021/acs.macromol.8b00741

  日期：2018.7.10

  The formation of intra- or intermolecular hydrogen bonding and their influences on polybenzoxazine's properties were investigated after the model benzoxazine monomers (o-AB-fbz, o-AF-fbz, o-AP-fbz, p-AB-fbz, p-AF-fbz, p-AP-fbz) were synthesized. Because of the different electron-donating abilities of bridging units (benzene, furan and pyridine) in isophthalic acid (IPA), 2,5-furandicarboxylic acid (2,5-FDCA) and 2,6-pyridinedicarboxylic acid (2,6-PDCA), the strength of intramolecular H-bonding involved with the oxygen atom in oxazine ring in o-AB-fbz, o-AF-fbz and o-AP-fbz followed the order of o-AB-fbz > o-AF-fbz > o-AP-fbz, and the strength of the overall H-bonding was arranged as follows: o-AB-fbz < o-AF-fbz < oAP-fbz. While more intermolecular H-bonding was formed in p-AB-fbz and p-AF-fbz as well as p-AP-fbz. DSC and FT-IR results discovered the relationship between the H-bonding involved with the oxygen atom in oxazine ring and the curing activities of benzoxazines. After curing reaction, the cured systems showed varied glass transition temperature (Tg), and the influence of H-bonding on Tg was revealed by in situ FT-IR analysis. Molecular dynamics (MD) simulation was also applied to investigate the properties of synthesized polybenzoxazines and similar results were obtained. Not only the formation of H-bonding but also their effects on both the curing behaviors of benzoxazine monomers and the thermal properties of cured resins were systematically investigated, which would help us understand polybenzoxazines more deeply and might be a guideline for improving their comprehensive properties only by manipulating the H-bonding.