N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide | 522602-90-0

• 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,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide
• 英文别名: N-[[4-[(pyridine-3-carbonylamino)methyl]phenyl]methyl]pyridine-3-carboxamide
• CAS: 522602-90-0
• 化学式: C₂₀H₁₈N₄O₂
• 分子量: 346.389
• InChiKey: BFSJSWOJYFBFBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 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：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以39%的产率得到Ag⁽¹⁺⁾*NO₃^(1-)*C₂₀H₁₈N₄O₂*CH₄O
  参考文献：
  名称：

  预组织或氢键不匹配：银（I）二酰胺配体配位聚合物与离散金属大环组件

  摘要：

  由于阴离子的重要环境、生物和药用作用，研究选择性复合阴离子的新基序是一个相当重要的领域。显示阴离子结合口袋的离散金属大环化合物或配位聚合物的合成可以从相对简单的成分中产生特定的阴离子受体。在这里，我们研究了一系列柔性二酰胺化合物 L1-L5 与银（I）金属盐的自组装。一种新的二酰胺配体，2,6-[N,N'-双（二-（吡啶-2-基）甲基）吡啶]-2,6-二甲酰胺（L5），具有两个螯合二-2-吡啶基甲基供体基团，也准备好了。化合物 L1–L3，缺乏中心 2,6-吡啶二甲酰胺核心的预组织作用，形成一维配位聚合物 {[Ag(L1)(CH3CN)](PF6)} n (6)，{[Ag(L2)](NO3)·(H2O)]} n (7) 和 {[AgNO3(L3)]·(CH3OH)]} n (9) 依次形成 2D 和 3D 氢键网络正交氢键。在一种情况下，L2 产生固态的双核金属大环，[Ag2(CF3CO2

  DOI：

  10.1080/10610278.2012.699052
• 作为产物：
  描述：

  1,4-苯二甲胺 、 氯化烟碱盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide
  参考文献：
  名称：

  Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding

  摘要：

  The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N'-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N'-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N'-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H center dot center dot center dot O=C hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N'-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N'-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N'-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N'-2'-propyl-6-(3-pyridylmethyl)pyrid me dicarboxamide 10 and N,N'-2'-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethyl amino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)-carbonyl] -2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.031

文献信息

• 双苄酰胺类CXCR4拮抗剂及其制备和应用
  申请人：杭州师范大学

  公开号：CN113845439A

  公开（公告）日：2021-12-28

  本发明公开了双苄酰胺类CXCR4拮抗剂及其制备方法和在制备抗炎、抗肿瘤、通过拮抗CXCR4靶点来防治相关疾病的药物中的应用。双苄酰胺类CXCR4拮抗剂为具有如下通式(I)或(II)的化合物和/或及其可药用盐：本发明采用简便高效的一步法合成了一系列新型的双苄酰胺类CXCR4拮抗剂，具有抗肿瘤、抗炎、抗感染、抗自身免疫等多种药理活性，在众多疾病中具有广泛的应用优势。
• Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding
  作者：Christopher J. Sumby、Lyall R. Hanton

  DOI：10.1016/j.tet.2009.04.031

  日期：2009.6

  The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N'-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N'-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N'-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H center dot center dot center dot O=C hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N'-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N'-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N'-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N'-2'-propyl-6-(3-pyridylmethyl)pyrid me dicarboxamide 10 and N,N'-2'-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethyl amino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)-carbonyl] -2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. (C) 2009 Elsevier Ltd. All rights reserved.
• Pre-organisation or a hydrogen bonding mismatch: silver(I) diamide ligand coordination polymers versus discrete metallo-macrocyclic assemblies
  作者：Maisara Abdul-Kadir、Philip R. Clements、Lyall R. Hanton、Courtney A. Hollis、Christopher J. Sumby

  DOI：10.1080/10610278.2012.699052

  日期：2012.8.1

  turn form 2D and 3D hydrogen-bonded networks through orthogonal hydrogen bonding. In one instance, L2 gives rise to a dinuclear metallo-macrocycle in the solid state, [Ag2(CF3CO2)2(L2)2][Ag2(μ2-CF3CO2)2(L2)2] (8). Both diamide ligands L4 and L5 form dinuclear metallo-macrocycles, [Ag2(NO2)2(L4)2] (10) and [Ag2(L5)2](NO3)2·2CH3OH·2H2O (11), in solution and in the solid state. Where possible, all compounds

  由于阴离子的重要环境、生物和药用作用，研究选择性复合阴离子的新基序是一个相当重要的领域。显示阴离子结合口袋的离散金属大环化合物或配位聚合物的合成可以从相对简单的成分中产生特定的阴离子受体。在这里，我们研究了一系列柔性二酰胺化合物 L1-L5 与银（I）金属盐的自组装。一种新的二酰胺配体，2,6-[N,N'-双（二-（吡啶-2-基）甲基）吡啶]-2,6-二甲酰胺（L5），具有两个螯合二-2-吡啶基甲基供体基团，也准备好了。化合物 L1–L3，缺乏中心 2,6-吡啶二甲酰胺核心的预组织作用，形成一维配位聚合物 [Ag(L1)(CH3CN)](PF6)} n (6)，[Ag(L2)](NO3)·(H2O)]} n (7) 和 [AgNO3(L3)]·(CH3OH)]} n (9) 依次形成 2D 和 3D 氢键网络正交氢键。在一种情况下，L2 产生固态的双核金属大环，[Ag2(CF3CO2