N²-(6-bromopyridine-2-yl)pyridine-2,6-diamine | 427900-26-3

• 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: N²-(6-bromopyridine-2-yl)pyridine-2,6-diamine
• 英文别名: N-(6'-bromopyrid-2'-yl)pyridine-2,6-diamine；N²-(6-bromopyridin-2-yl)pyridine-2,6-diamine；bromo-H3dpda；N2-(6-Bromopyridin-2-yl)pyridine-2,6-diamine；6-N-(6-bromopyridin-2-yl)pyridine-2,6-diamine
• CAS: 427900-26-3
• 化学式: C₁₀H₉BrN₄
• 分子量: 265.112
• InChiKey: HCBVZHGTSIXLHD-UHFFFAOYSA-N

物化性质

• 沸点：
  404.2±45.0 °C(Predicted)
• 密度：
  1.652±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²-(6-bromopyridine-2-yl)pyridine-2,6-diamine 以 氯仿 为溶剂， 反应 12.0h， 生成 N-(4-chlorophenyl)-N’-(6-{[6-(pyrrolidin-1-yl)pyridin-2-yl]amino}pyridin-2-yl)urea
  参考文献：
  名称：

  PSNCBAM-1 analogs: Structural evolutions and allosteric properties at cannabinoid CB1 receptor

  摘要：

  Allosteric modulation of the CB1Rs could represent an alternative strategy for the treatment of diseases in which these receptors are involved, without the undesirable effects associated with their orthosteric stimulation. PSNCBAM-1 is a reference diaryl urea derivative that positively affects the binding affinity of orthosteric ligands (PAM) and negatively affects the functional activity of orthosteric ligands (NAM) at CB1Rs. In this work we reported the design, synthesis and biological evaluation of three different series of compounds, derived from structural modifications of PSNCBAM-1 and its analogs reported in the recent literature. Almost all the new compounds increased the percentage of binding affinity of CP55940 at CB1Rs, showing a PAM profile. When tested alone in the [ 35 S]GTPyS functional assay, only a few derivatives lacked detectable activity, so were tested in the same functional assay in the presence of CP55940. Among these, compounds 11 and 18 proved to be functional NAMs at CB1Rs, dampening the orthosteric agonist-induced receptor functionality by approximately 30%. The structural features presented in this work provide new CB1R-allosteric modulators (with a profile similar to the reference compound PSNCBAM-1) and an extension of the structure-activity relationships for this type of molecule at CB1Rs. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112606
• 作为产物：
  描述：

  2,6-二氨基吡啶 、 2,6-二溴吡啶 在 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以94%的产率得到N²-(6-bromopyridine-2-yl)pyridine-2,6-diamine
  参考文献：
  名称：

  Manipulation of electronic structure via supporting ligands: a charge disproportionate model within the linear metal framework of asymmetric nickel string [Ni7(phdptrany)4Cl](PF6)

  摘要：

  本文介绍了一种独特的不对称庚镍弦络合物的合成和物理性质，该络合物沿线性镍框架呈现出电荷比例失调模型。

  DOI：

  10.1039/b926315b

文献信息

• Methylazacalixpyridines: Remarkable Bridging Nitrogen-Tuned Conformations and Cavities with Unique Recognition Properties
  作者：Han-Yuan Gong、Xiao-Hang Zhang、De-Xian Wang、Hong-Wei Ma、Qi-Yu Zheng、Mei-Xiang Wang

  DOI：10.1002/chem.200600377

  日期：2006.12.13

  methylazacalix[4]arene[4]pyridine interact efficiently with fullerenes C(60) and C(70) through van der Waals forces. Their ease of preparation, versatile conformational structures, and recognition properties make these multinitrogen-containing calixarenes or cyclophanes unique and powerful macrocyclic hosts in supramolecular chemistry.

  甲基氮杂aca啶[n]吡啶（n = 4、8）和甲基氮杂lix杂[m]芳烃[n]吡啶（m = n = 2、4）是通过一种方便的片段偶联方法从2,6-二溴吡啶，2开始合成的。 6-二氨基吡啶和苯-1,3-二胺。由于氮的内在电子性质，它可以主要通过sp（2）杂交，使其与相邻的一个或两个吡啶环进行各种共轭，部分共轭或不共轭，因此，氮桥联的杯吡啶吡啶衍生物可作为氮原子一类独特的大环宿主分子，具有有趣的构象结构，可提供微调的腔体和通用的识别特性。在溶液中是通量的，在固态甲基氮杂az [4]吡啶中采用1，具有C（2v）对称性的3个交替构型，其中每两个桥接氮原子与一个吡啶环共轭。质子化后，甲基azacalix [4]吡啶物种具有四个共轭氮原子的不同共轭体系，产生具有近似S（4）对称性的相似的扭曲1,3-交替构象。每个质子化的甲基氮杂acalix [4]吡啶的腔体，以适应不同大小和几何形状，如平面DMF或H
• Probing the electronic communication of linear heptanickel and nonanickel string complexes by utilizing two redox-active [Ni2(napy)4]3+ moieties
  作者：Shao-An Hua、Isiah Po-Chun Liu、Hasan Hasanov、Gin-Chen Huang、Rayyat Huseyn Ismayilov、Chien-Lan Chiu、Chen-Yu Yeh、Gene-Hsiang Lee、Shie-Ming Peng

  DOI：10.1039/b923125k

  日期：——

  Two extended nickel string complexes, [Ni7(bnapy)4Cl2](Cl)2 (2) and [Ni9(bnapya)4Cl2](PF6)2 (3) (bnapy2− = 2,6-bis(1,8-naphthyridylamido)pyridine and bnapya3- = bis(6-(1,8-naphthyridylamido)pyridyl)amido), which possess two redox-active [Ni2(napy)4]3+ units, were synthesized and characterized. The electronic communication between the two redox-active units in both complexes can be investigated not only by magnetic measurements but also by analyzing the difference between two consecutive one-electron oxidation peaks (ΔE1/2) of 2 and 3. The antiferromagnetic coupling between the two [Ni2(napy)4]3+ fragments become weaker as the metal frameworks are elongated (J = −13.21 and −1.48 cm−1 for 2 and 3, respectively). Moreover, the ΔE1/2 values of 2 and 3 are 110 and 84 mV, respectively, which are smaller than that (300 mV) of their pentanickel analogue [Ni5(bna)4(Cl)2](PF6)2 (bna− = bisnaphthyridylamido) (1). These ΔE1/2 values indicate that the electronic communication decreases with increasing number of inner diamagnetic nickel ions in nickel string complexes.

  两个延伸的镍串络合物，[Ni7(bnapy)4Cl2](Cl)2 (2) 和 [Ni9(bnapya)4Cl2](PF6)2 (3) (bnapy2− = 2,6-bis(1,8-naphthyridylamido) ) 吡啶和 bnapya3- = 双(6-(1,8-萘啶基酰胺基)吡啶基)酰胺基) 具有两个氧化还原活性 [Ni2(napy)4]3+ 单元，已合成并表征。两种复合物中两个氧化还原活性单元之间的电子通信不仅可以通过磁性测量来研究，还可以通过分析 2 和 3 的两个连续单电子氧化峰 (ΔE1/2) 之间的差异来研究。随着金属骨架的拉长，两个 [Ni2(napy)4]3+ 片段变得更弱（对于 2 和 3，分别为 J = -13.21 和 -1.48 cm−1）。此外，2和3的ΔE1/2值分别为110和84 mV，小于其五镍类似物[Ni5(bna)4(Cl)2](PF6)2 (bna− = 双萘啶酰氨基) (1)。这些 ΔE1/2 值表明电子通讯随着镍串复合物中内部反磁性镍离子数量的增加而减少。
• Self-Complementarity of Oligo-2-aminopyridines:  A New Class of Hydrogen-Bonded Ladders
  作者：Man-kit Leung、Ashis B. Mandal、Chih-Chieh Wang、Gene-Hsiang Lee、Shie-Ming Peng、Hsing-Ling Cheng、Guor-Rong Her、Ito Chao、Hsiu-Feng Lu、Ying-Chieh Sun、Mei-Ying Shiao、Pi-Tai Chou

  DOI：10.1021/ja011679p

  日期：2002.4.1

  A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization, Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest-host molecules.
• Synthesis of long-chained oligo-α-aminopyridines by tandem Pd-catalyzed cross-coupling aminations and their helical dinuclear complexes
  作者：Hasan Hasanov、Uan-Kang Tan、Rui-Ren Wang、Gene Hsiang Lee、Shie-Ming Peng

  DOI：10.1016/j.tetlet.2004.08.066

  日期：2004.10

  Three novel multidentate long-chained oligo-alpha-aminopyridine ligands, nonapyridyloctaamine (1, npoa), decapyridyinonaamine (2, dpna), and undecapyridyldecaamine (3, upda) were synthesized successfully by tandem Pd-catalyzed cross-coupling aminations. The helical structures of protonated ligand npoa 4, [H(4)npoa](SO3CF3)(4)} and the related dinuclear complexes 5-10 were synthesized and characterized by X-ray diffractions. (C) 2004 Elsevier Ltd. All rights reserved.