4-formyl-1-methylquinolin-1-ium iodide | 94442-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-formyl-1-methylquinolin-1-ium iodide
• 英文别名: 4-formyl-1-methylquinolinium iodide
• CAS: 94442-49-6
• 化学式: C₁₁H₁₀NO*I
• 分子量: 299.111
• InChiKey: VQNQQQPPTQLAHN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.52
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.95
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-formyl-1-methylquinolin-1-ium iodide 、 pyrazine-2,6-dicarbohydrazide 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 以89 %的产率得到N′²,N′⁶-bis[(1-methylquinolinium-4-yl)methylene]pyrazine-2,6-dicarbohydrazideiodide
  参考文献：
  名称：

  通过阳离子双（酰腙）的平行合成和筛选相结合的 SAR 研究优化 G-四联体配体

  摘要：

  准备放映。通过直接缩合相应的结构单元来制备作为推定 G4-DNA 配体的阳离子双（酰基腙）文库。通过荧光熔解实验筛选所得样品（无需任何分离或纯化步骤），确定了三种新的靶标，并通过多种生物物理方法和分子建模详细研究了它们与 G4-DNA 靶标的相互作用。

  DOI：

  10.1002/chem.202202427
• 作为产物：
  描述：

  4-喹啉甲醛 、 碘甲烷 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-formyl-1-methylquinolin-1-ium iodide
  参考文献：
  名称：

  隐藏的签名：用于开发潜在指纹的新试剂†

  摘要：

  已经研究了用季铵化吡啶鎓或喹啉鎓环取代的醛用于潜在指纹的形成。开发了两种途径以形成新颖的原位形成的杜鹃花青染料。这种染料可能会在浓缩试剂的指纹图中形成，但在溶液实验中不会明显形成，这是由于在600 nm处没有吸收带所证明的。N-烷基和N-芳基取代的苯并咪唑-2-甲醛具有稳定的荧光指纹。

  DOI：

  10.1039/b820257e

文献信息

• Quadruplex DNA-guided ligand selection from dynamic combinatorial libraries of acylhydrazones
  作者：Oksana Reznichenko、Anne Cucchiarini、Valérie Gabelica、Anton Granzhan

  DOI：10.1039/d0ob01908a

  日期：——

  Dynamic combinatorial libraries of acylhydrazones were prepared from diacylhydrazides and several cationic or neutral aldehydes in the presence of 5-methoxyanthranilic acid catalyst. Pull-down experiments with magnetic beads functionalized with a G-quadruplex (G4)-forming oligonucleotide led to the identification of putative ligands, which were resynthesized or emulated by close structural analogues

  在5-甲氧基邻氨基苯甲酸催化剂存在下，由二酰肼和几种阳离子或中性醛制备酰基的动态组合库。用形成G-四链体（G4）的寡核苷酸功能化的磁珠的下拉实验导致推定的配体的鉴定，这些配体由紧密的结构类似物重新合成或模拟。通过荧光滴定，质谱和热变性实验评估了新型衍生物的G4结合特性，从而证明了两种化合物具有强结合力（K d <10 nM）。
• Novel cationic bis(acylhydrazones) as modulators of Epstein–Barr virus immune evasion acting through disruption of interaction between nucleolin and G-quadruplexes of EBNA1 mRNA
  作者：Oksana Reznichenko、Alicia Quillévéré、Rodrigo Prado Martins、Nadège Loaëc、Hang Kang、María José Lista、Claire Beauvineau、Jorge González-García、Régis Guillot、Cécile Voisset、Chrysoula Daskalogianni、Robin Fåhraeus、Marie-Paule Teulade-Fichou、Marc Blondel、Anton Granzhan

  DOI：10.1016/j.ejmech.2019.05.042

  日期：2019.9

  The oncogenic Epstein-Barr virus (EBV) evades the immune system through limiting the expression of its highly antigenic and essential genome maintenance protein, EBNA1, to the minimal level to ensure viral genome replication, thereby also minimizing the production of EBNA1-derived antigenic peptides. This regulation is based on inhibition of translation of the virally-encoded EBNA1 mRNA, and involves the interaction of host protein nucleolin (NCL) with G-quadruplex (G4) structures that form in the glycine-alanine repeat (GAr)-encoding sequence of the EBNA1 mRNA. Ligands that bind to these G4-RNA can prevent their interaction with NCL, leading to disinhibition of EBNA1 expression and antigen presentation, thereby interfering with the immune evasion of EBNA1 and therefore of EBV (M.J. Lista et al., Nature Commun., 2017, 8, 16043). In this work, we synthesized and studied a series of 20 cationic bis(acylhydrazone) derivatives designed as G4 ligands. The in vitro evaluation showed that most derivatives based on central pyridine (Py), naphthyridine (Naph) or phenanthroline (Phen) units were efficient G4 binders, in contrast to their pyrimidine (Pym) counterparts, which were poor G4 binders due to a significantly different molecular geometry. The influence of lateral heterocyclic units (N-substituted pyridinium or quinolinium residues) on G4-binding properties was also investigated. Two novel compounds, namely PyDH2 and PhenDH2, used at a 5 μM concentration, were able to significantly enhance EBNA1 expression in H1299 cells in a GAr-dependent manner, while being significantly less toxic than the prototype drug PhenDC3 (GI₅₀ > 50 μM). Antigen presentation, RNA pull-down and proximity ligation assays confirmed that the effect of both drugs was related to the disruption of NCL-EBNA1 mRNA interaction and the subsequent promotion of GAr-restricted antigen presentation. Our work provides a novel modular scaffold for the development of G-quadruplex-targeting drugs acting through interference with G4-protein interaction.