2-bromo-5-(5-bromo-3-methyl-2-pyridyl)-3-methylpyridine | 1175709-62-2

• 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: 2-bromo-5-(5-bromo-3-methyl-2-pyridyl)-3-methylpyridine
• 英文别名: 5,6'-dibromo-3,5'-dimethyl-[2,3']bipyridine；5-bromo-6'-iodo-3,5'-dimethyl-2,3'-bipyridine；2-Bromo-5-(5-bromo-3-methylpyridin-2-yl)-3-methylpyridine；2-bromo-5-(5-bromo-3-methylpyridin-2-yl)-3-methylpyridine
• CAS: 1175709-62-2
• 化学式: C₁₂H₁₀Br₂N₂
• 分子量: 342.033
• InChiKey: IYYVAWIFEBAMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(5-bromo-3-methyl-2-pyridyl)-3-methylpyridine 在 四(三苯基膦)钯 、 sodium carbonate 、 乙酰氯 、 sodium iodide 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 76.0h， 生成 5,6'''-dibromo-3,5',5'',5'''-tetramethyl-[2,3';6',3'';6'',3''']quaterpyridine
  参考文献：
  名称：

  芳香花环，作为新的折叠子，模仿蛋白质的二级结构

  摘要：

  蛋白质调节所有生物功能的大部分，并且由高度组织化的二级结构元素（例如，螺旋，弯角和薄片）组成。这些功能中的许多功能都受到少数关键结构元素（蛋白质与蛋白质的相互作用）的影响。通过肽和非肽支架模仿它们已成为当代研究的主要焦点。本文将寡聚体系统视为新的折叠子，它们可以复制螺旋的局部形貌，或以类似于α-螺旋残基的方式投射适当的功能。

  DOI：

  10.1016/j.tet.2012.02.035
• 作为产物：
  描述：

  2,5-二溴-3-甲基吡啶 、 6-溴-5-甲基吡啶-3-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以15%的产率得到2-bromo-5-(5-bromo-3-methyl-2-pyridyl)-3-methylpyridine
  参考文献：
  名称：

  Synthesis of dihalo bi- and terpyridines by regioselective Suzuki–Miyaura cross-coupling reactions

  摘要：

  This paper describes ail efficient and regioselective synthetic route leading to new dihalobi- and terpyridines. We developed a strategy based on regioselective sequence of Suzuki-Miyaura cross-coupling reactions between bromopyridyl boronic acids and dihalopyridines and dihalobipyridines. The study of the influence of the nature and the position of the halogen atoms leads to prepare bromoiododerivatives to obtain good selectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.049

文献信息

• Synthesis of Pyridoclax Analogues: Insight into Their Druggability by Investigating Their Physicochemical Properties and Interactions with Membranes
  作者：Martina De Pascale、Domenico Iacopetta、Marc Since、Sophie Corvaisier、Véronique Vie、Gilles Paboeuf、Didier Hennequin、Serge Perato、Marcella De Giorgi、Maria Stefania Sinicropi、Jana Sopkova‐De Oliveira Santos、Anne‐Sophie Voisin‐Chiret、Aurélie Malzert‐Freon

  DOI：10.1002/cmdc.201900542

  日期：2020.1.7

  anticancer drug, acting as a protein-protein interaction disruptor, with potential applications in the treatment of ovarian, lung, and mesothelioma cancers. Eighteen sensibly selected structural analogues of Pyridoclax were synthesized, and their physicochemical properties were systematically assessed and analyzed. Moreover, considering that drug-membrane interactions play an essential role in understanding

  Pyridoclax被认为是一种有前途的抗癌药物，可作为蛋白质-蛋白质相互作用破坏剂，在卵巢癌，肺癌和间皮瘤癌症的治疗中具有潜在的应用。合成了十八个Pyridoclax的明智选择的结构类似物，并对其物理化学性质进行了系统的评估和分析。此外，考虑到药物-膜相互作用在理解给定药物的作用方式及其最终毒性作用中起着至关重要的作用，因此使用膜模型研究了散装（脂质体）和空气-水界面的相互作用。在所有原始低聚吡啶上测得的实验数据可以评估理化性质方面的相对差异，这可以决定其可药物性，从而决定药物的开发。
• Synthesis of new linear poly(phenylpyridyl) chains
  作者：Serge Perato、Anne Sophie Voisin-Chiret、Jana Sopková-de Oliveira Santos、Rémi Legay、Hassan Oulyadi、Sylvain Rault

  DOI：10.1016/j.tet.2011.12.074

  日期：2012.2

  This paper describes for the first time an efficient approach of Suzuki Miyaura cross-coupling reaction leading to new mixed linear unsymmetric phenylpyridyl chains (garlands). We have studied the synthesis of new phenylpyridyl boronic species and their reactivity with a dihalogenated bipyridine to obtain four and six unit phenylpyridines. (C) 2011 Elsevier Ltd. All rights reserved.
• Structural Characterizations of Oligopyridyl Foldamers, α-Helix Mimetics
  作者：Jana Sopkova-de Oliveira Santos、Anne Sophie Voisin-Chiret、Gregory Burzicki、Laure Sebaoun、Muriel Sebban、Jean-François Lohier、Rémi Legay、Hassan Oulyadi、Ronan Bureau、Sylvain Rault

  DOI：10.1021/ci200424a

  日期：2012.2.27

  Protein-protein interactions are central to many biological processes, from intracellular communication to cytoskeleton assembly, and therefore represent an important class of targets for new therapeutics. The most common secondary structure in natural proteins is an alpha-helix. Small molecules seem to be attractive candidates for stabilizing or disrupting protein protein interactions based on alpha-helices. In our study, we assessed the ability of oligopyridyl scaffolds to mimic the alpha-helical twist. The theoretical as well as experimental studies (X-ray diffraction and NMR) on conformations of bipyridines in the function of substituent and pyridine nitrogen positions were carried out. Furthermore, the experimental techniques showed that the conformations observed in bipyridines are maintained within a longer oligopyridyl scaffold (quaterpyridines). The alignment of the synthesized quaterpyridine with two methyl substituents showed that it is an alpha-helix foldamer; their methyl groups overlap very well with side chain positions, i and i + 3, of an ideal alpha-helix.