2,6-bis<4-(bromomethyl)phenyl>pyridine | 97431-84-0

• 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: 2,6-bis<4-(bromomethyl)phenyl>pyridine
• 英文别名: 2,6-Bis[4-(bromomethyl)phenyl]pyridine
• CAS: 97431-84-0
• 化学式: C₁₉H₁₅Br₂N
• 分子量: 417.143
• InChiKey: GRXNSVFZNLHBCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-bis<4-(bromomethyl)phenyl>pyridine 、 2,2'-<1,2-Phenylenbis(oxy-2,1-ethandiyloxy)>bisphenol 在 CsCO₃ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 12,19,22,29,32,39-hexaoxa-48-azaheptacyclo[39.2.2.27,10.12,6.013,18.023,28.033,38]octatetraconta-1(43),2(48),3,5,7(47),8,10(46),13,15,17,23,25,27,33,35,37,41,44-octadecaene
  参考文献：
  名称：

  Solid-state inclusion compounds of new host macrocycles with uncharged organic molecules. Host synthesis, inclusion properties, and x-ray crystal structure of an inclusion compound with n-propanol

  摘要：

  DOI：

  10.1021/jo00217a022
• 作为产物：
  描述：

  2,6-双(对-甲基苯)吡啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 36.0h， 以62%的产率得到2,6-bis<4-(bromomethyl)phenyl>pyridine
  参考文献：
  名称：

  Quantitative structure-activity relationship analysis of cation-substituted polyaromatic compounds as potentiators (amplifiers) of bleomycin-mediated degradation of DNA

  摘要：

  A set of 21 polyheteroaromatic compounds substituted with flexible cationic groups and of similar molecular size has been analyzed for binding with DNA and for effects on the bleomycin-mediated degradation of the DNA double helix. Increases in apparent rates of the DNA digestion were observed in all cases under the experimental conditions of noncompetitive binding of these compounds and bleomycin to DNA. Surprisingly, the quantitative structure-activity relationship analysis revealed two distinct correlations despite close structural similarities for the set of bleomycin amplifiers. These unusual results are explained in terms of the formation of two stereochemically different ternary complexes of activated bleomycin-DNA-amplifier. The relevance of this finding for the design of new bleomycin amplifiers is discussed.

  DOI：

  10.1021/jm00106a017

文献信息

• Synthesis, Molecular Modeling, and Pharmacological Testing of Bis-Quinolinium Cyclophanes:  Potent, Non-Peptidic Blockers of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channel
  作者：Joaquin Campos Rosa、Dimitrios Galanakis、Alessandro Piergentili、Kalpana Bhandari、C. Robin Ganellin、Philip M. Dunn、Donald H. Jenkinson

  DOI：10.1021/jm9902537

  日期：2000.2.1

  the blocking potency changes dramatically with simple structural variations in the linkers. One of these smaller cyclophanes having A = benzene-1,4-diylbis(methylene) and L = benzene-1, 3-diylbis(methylene) (3j, 6,10-diaza-1,5(1,4)-diquinolina-3(1,3),8(1, 4)-dibenzenacyclodecaphanedium tritrifluoroacetate, UCL 1684) has an IC(50) of 3 nM and is the most potent non-peptidic SK(Ca) channel blocker described

  提出了合成和药理学测试的两个系列的双双喹啉鎓环烷作为对罂粟碱敏感的Ca（2+）激活的K（+）（SK（Ca））通道的阻滞剂。在这些环芳基中，两个4-氨基喹啉基在环的N原子（接头L）和环外的N原子（接头A）处连接。在A和L各自含有两个或更多个芳环的那些情况下，化合物的活性并不严格取决于连接基的性质。当A和L各自仅具有一个苯环时，通过连接基中的简单结构变化，封端效力急剧变化。这些较小的环烷中的一个具有A =苯-1,4-二基双（亚甲基），L =苯-1,3-二基双（亚甲基）（3j，6,10-diaza-1,5（1,4）-diquinolina -3（1,3），8（1，4）-二苯甲环环癸酸三氟乙酸酯，UCL 1684）的IC（50）为3 nM，是迄今为止描述的最有效的非肽SK（Ca）通道阻滞剂。使用分子建模技术对较小的Cyclphanes进行构象分析表明，该化合物的封闭能力不同可能归因于其不同的构象偏好。
• Synthesis, Molecular Modeling, and K⁺ Channel-Blocking Activity of Dequalinium Analogues Having Semirigid Linkers
  作者：Joaquin Campos Rosa、Dimitrios Galanakis、C. Robin Ganellin、Philip M. Dunn

  DOI：10.1021/jm950884a

  日期：1996.1.1

  Dequalinium [1,1'-(decane-1, 10-diyl)bis(2-methyl-4-aminoquinolinium)] is an effective blocker of the small conductance Ca2(+)-activated K+ channel. It has been shown that the number of methylene groups in the alkyl chain linking the two quinolinium rings of this type of molecule is not critical for activity. To further investigate the role of the linker, analogues of dequalinium have been synthesized

  角鲨烯[1,1'-（癸烷-1，10-二基）双（2-甲基-4-氨基喹啉）]是小电导Ca2（+）激活的K +通道的有效阻滞剂。已经表明，在连接这种类型的分子的两个喹啉鎓环的烷基链中的亚甲基的数目对于活性不是关键的。为了进一步研究接头的作用，已合成了癸胺盐的类似物，其中烷基链已被 X 取代，其中X是含有芳香环的刚性或半刚性基团。已经测试了该化合物对大鼠交感神经元缓慢的超极化后的阻滞作用。最有效的化合物为X =菲基，芴基，顺二苯乙烯和C6H4（CH2）n ，其中n = 0-4。使用XED / COSMIC分子建模系统研究了化合物的构象偏好。尽管类似物的效力对接头（X）的构象性质有一定的依赖性，但是总体上，具有实质性结构差异的X基团是可容忍的。X似乎为两个喹啉基团提供了支持，并且不直接与通道相互作用。刚性基团X提供的喹啉鎓环之间的分子内间隔对于活性不是关键。这可能归因于杂环的残留构象迁
• Mehta, Lina K.; Parrick, John; Sadiq, Samina, Journal of Chemical Research, Miniprint, 2000, # 11, p. 1221 - 1236
  作者：Mehta, Lina K.、Parrick, John、Sadiq, Samina

  DOI：——

  日期：——
• Self-Complementary [2]Catenanes and Their Related [3]Catenanes
  作者：Beatriz Cabezon、Jianguo Cao、Françisco M. Raymo、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1002/1521-3765(20000616)6:12<2262::aid-chem2262>3.0.co;2-g

  日期：2000.6.16

  Three [3]catenanes with cavities large enough to accommodate aromatic guests have been designed and synthesized (yields = 5-20 %) by means of kinetically controlled self-assembly processes The X-ray structural analysis of one of three [3]catenanes confirmed the presence of a rectangular cavity (dimensions = 7 x 11 Angstrom) lined by pi-electron-rich recognition sites and hydrogen-bond acceptor groups. Ln spite of their apparently ideal recognition features, none of these [3]catenanes bind guests incorporating a pi-electron-deficient bipyridinium unit. However, the template-directed syntheses of the [3]catenanes also produce, in yields of 2-23%, [2]catenanes incorporating a 1,5-dioxynaphtho[38]crown-10 interlocked with a bipyridinium-based tetracationic cyclophane. The X-ray structural analyses of two of these [2]catenanes revealed that a combination of [pi ... pi] and [C-H ... pi] interactions is responsible for the formation of supramolecular homodimers in the solid state. H-1 NMR spectroscopic investigations of the four [2]catenanes demonstrated that supramolecular homodimers are also formed (K-a-17-31 M-1, T = 185 K) in (CD3)(2)CO solutions. Dynamic H-1 NMR spectroscopy revealed that the 1,5-dioxynaphtho[38]crown-10 and tetracationic cyclophane components in the four [2]catenanes and in the three [3]catenanes circumrotate: (Delta G(c)* = 9-14 kcal mol(-1)) through each other's cavity in (CD3)(2)CO. Similarly, the 1,5-dioxynaphthalene and the bipyridinium ring systems rotate (Delta G(c)* = 10-14 kcal mol(-1)) about their [O ... O] and [N ... N] axes, respectively, in solution.
• STREKOWSKI, LUCJAN;WILSON, W. DAVID;MOKROSZ, JERZY L.;MOKROSZ, MARIA J.;H+, J. MEC. CHEM., 34,(1991) N, C. 580-588
  作者：STREKOWSKI, LUCJAN、WILSON, W. DAVID、MOKROSZ, JERZY L.、MOKROSZ, MARIA J.、H+

  DOI：——

  日期：——