2,6-bis((4-methoxybenzene)carbamoyl)pyridine | 126230-10-2

• 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-methoxybenzene)carbamoyl)pyridine
• 英文别名: 2,6-(4-CH3OC6H4NHCO)2C5H3N；N,N'-bis(4-methoxyphenyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis(4-methoxyphenyl)pyridine-2,6-dicarboxamide
• CAS: 126230-10-2
• 化学式: C₂₁H₁₉N₃O₄
• mdl: MFCD02087076
• 分子量: 377.4
• InChiKey: LUARIMMADZPWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis((4-methoxybenzene)carbamoyl)pyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以60%的产率得到2,6-bis((4-hydroxybenzene)carbamoyl)pyridine
  参考文献：
  名称：

  Syntheses, characterization, and anti-cancer activities of pyridine-amide based compounds containing appended phenol or catechol groups

  摘要：

  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。

  DOI：

  10.1007/s12039-014-0671-3
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 、 甲氧苯胺 在 亚磷酸三苯酯 作用下， 生成 2,6-bis((4-methoxybenzene)carbamoyl)pyridine
  参考文献：
  名称：

  Syntheses, characterization, and anti-cancer activities of pyridine-amide based compounds containing appended phenol or catechol groups

  摘要：

  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。

  DOI：

  10.1007/s12039-014-0671-3

文献信息

• Facile Preparation of 6-Bromopyridine-2-carboxamide and Pyridine-2,6-dicarboxamide: Partial Aminocarbonylation of 2,6-Dibromopyridine
  作者：Hiroshi Horino、Hiroyuki Sakaba、Mannosuke Arai

  DOI：10.1055/s-1989-27372

  日期：——

  The palladium-catalyzed carbonylation of 2,6-dibromopyridine in the presence of primary amines under controlled conditions (carbon monoxide pressure) gives mainly N-aryl- or N-alkyl-6-bromopyridine-2-carboxamides accompanied by N,N′-diaryl- or N,N′-dialkylpyridine- 2,6-dicarboxamides. Further aminocarbonylation of the N-aryl- and N- alkyl-6-bromopyridine-2-carboxamides affords unsymmetric N,N′- diaryl, N-alkyl-N′-aryl-, or N,N′-dialkylpyridine-2,6-dicarboxamides.

  在受控条件下（如一氧化碳压力）下，钯催化的2,6-二溴吡啶与初级胺的羰基化反应主要生成N-芳基或N-烷基-6-溴吡啶-2-羧酰胺，并伴有N,N′-二芳基或N,N′-二烷基吡啶-2,6-二羧酰胺。对N-芳基和N-烷基-6-溴吡啶-2-羧酰胺进行进一步的氨基羰基化反应，可以得到不对称的N,N′-二芳基、N-烷基-N′-芳基或N,N′-二烷基吡啶-2,6-二羧酰胺。
• Hydroxide-bridged dicopper complexes: the influence of secondary coordination sphere on structure and catecholase activity
  作者：Deepak Bansal、Rajeev Gupta

  DOI：10.1039/c6dt04858g

  日期：——

  to them have been used for the synthesis of dicopper(II) complexes 1–6 having a Cu(μ-OH)Cu core. The crystal structures of 1–6 show that while every Cu(II) ion is ligated within the N3 pincer cavity of a potentially multidentate ligand, two Cu(II) centers are bridged by a hydroxide group. Notably, the Cu(μ-OH)Cu core is encased within the secondary coordination sphere intricately created by the appended

  酰胺基配体（H 2 L 1–6）上附加有各种官能团，已用于合成具有Cu（μ-OH）Cu核的dicopper（II）配合物1-6。1–6的晶体结构表明，尽管每个Cu（II）离子都连接在一个潜在的多齿配体的N 3钳形腔内，但两个Cu（II）中心却被一个氢氧基团桥接。值得注意的是，Cu（μ-OH）Cu核被包裹在由附加基团复杂创建的次级配位球内。配合物1和2表现出在Cu（μ-OH）Cu核附近存在H键受体，配合物3和4显示在H原子附近存在H键供体以及H键受体基团Cu（μ-OH）Cu核。相比之下，配合物5和6在Cu（μ-OH）Cu核周围呈现修饰的二级配位球，其中5个中的H键相互作用基团有限，而6个中没有此类基团。我们表明，附加基团的氢键结合程度不仅调节Cu-OH键距，Cu（μ-OH）Cu角和Cu-Cu分离度，而且还调节Cu 2+ / Cu +氧化还原电位。所有六个复合物均具有氧化3,5-二叔丁基邻苯二
• Anion Complexation and Transport by Isophthalamide and Dipicolinamide Derivatives: DNA Plasmid Transformation in <i>E. coli</i>
  作者：Jason L. Atkins、Mohit B. Patel、Megan M. Daschbach、Joseph W. Meisel、George W. Gokel

  DOI：10.1021/ja304816e

  日期：2012.8.22

  Tris-arenes based on either isophthalic acid or 2,6-dipicolinic acid have been known for more than a decade to bind anions. Recent studies have also demonstrated their ability to transport various ions through membranes. In this report, we demonstrate two important properties of these simple diamides. First, they transport plasmid DNA into Escherichia colt about 2-fold over controls, where the ampicillin resistance gene is expressed in the bacteria. These studies were done with plasrnid DNA (similar to 2.6 kilobase (kb)) in JM109 E. coli cells. Second, known methods do not typically transport large plasmids (>15 kb). We demonstrate here that transformation of large pVIB plasmids (i.e., >20 kb) were enhanced over water controls by similar to 10-fold. These results are in striking contrast to the normal decrease in transformation with increasing plasmid size.
• Chemical Mustard Containment Using Simple Palladium Pincer Complexes: The Influence of Molecular Walls
  作者：Qi-Qiang Wang、Rowshan Ara Begum、Victor W. Day、Kristin Bowman-James

  DOI：10.1021/ja408770u

  日期：2013.11.13

  Six amide-based NNN palladium(II) pincer complexes Pd(L)(CH3CN) were synthesized, characterized, and examined for binding the sulfur mustard surrogate, 2-chloroethyl ethyl sulfide (CEES). The complexes all bind readily with CEES as shown by 'H NMR spectroscopy in CDCl3. The influence of parasubstituents on the two amide phenyl appendages was explored as well as the effect of replacing the phenyl groups with larger aromatic rings, 1-naphthalene and 9-anthracene. While variations of the parasubstituents had only a slight influence on the binding affinities, incorporation of larger aromatic rings resulted in a significant size-related increase in binding, possibly due to increasing steric and electronic interactions. In crystal structures of three CEES-bound complexes, the mustard binds through the sulfur atom and lies along the aromatic walls of the side appendages approximately perpendicular to the pincer plane, with increasingly better alignment progressing from phenyl to 1-naphthalene to 9-anthracene.
• N,N′-Bis(aryl)pyridine-2,6-dicarboxamide complexes of ruthenium: Synthesis, structure and redox properties
  作者：Moutusi Dasgupta、Sumon Nag、Gopal Das、Munirathinam Nethaji、Samaresh Bhattacharya

  DOI：10.1016/j.poly.2007.08.042

  日期：2008.1

  Reaction of five N,N'-bis(aryl)pyridine-2,6-dicarboxamides (H2L-R, where H-2 denotes the two acidic protons and R (R = OCH3, CH3, H, Cl and NO2) the para substituent in the aryl fragment) with [Ru(trpy)Cl-3](trpy = 2,2',2"-terpyridine) in refluxing ethanol in the presence of a base (NEW affords a group of complexes of the type [Ru-II(trpy)(L-R)], each of which contains an amide ligand coordinated to the metal center as a dianionic tridentate N,N,N-donor along with a terpyridine ligand. Structure of the [Ru-II(trpy)(L-Cl)] complex has been determined by X-ray crystallography. All the Ru(II) complexes are diamagnetic, and show characteristic H-1 NMR signals and intense MLCT transitions in the visible region. Cyclic voltammetry on the [Ru-II(trpy)(L-R)] complexes shows a Ru(II)-Ru(III) oxidation within 0.16-0.33 V versus SCE. An oxidation of the coordinated amide ligand is also observed within 0.94-1.33 V versus SCE and a reduction of coordinated terpyridine ligand within -1.10 to -1.15 V versus SCE. Constant potential coulometric oxidation of the [Ru-II(trpy)(L-R)] complexes produces the corresponding [Ru-II(trpy)(L-R)](+) complexes, which have been isolated as the perchlorate salts. Structure of the [Ru-III(trpy)(L-CH3)ClO4 complex has been determined by X-ray crystallography. All the Ru(Ill) complexes are one-electron paramagnetic, and show anisotropic ESR spectra at 77 K and intense LMCT transitions in the visible region. A weak ligand-field band has also been shown by all the [Ru-III(trpy)(L-R)]ClO4 complexes near 1600 nm. (C) 2007 Elsevier Ltd. All rights reserved.