1,2-dimethyl-4-iodo-quinolin-1-ium chloride | 1435944-69-6

• 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: 1,2-dimethyl-4-iodo-quinolin-1-ium chloride
• 英文别名: 4-Iodo-1,2-dimethylquinolin-1-ium;chloride
• CAS: 1435944-69-6
• 化学式: C₁₁H₁₁IN*Cl
• 分子量: 319.573
• InChiKey: BHUDANOZNBQEIY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-4-iodo-quinolin-1-ium chloride 、 4-二苯胺基苯甲醛 、 1,2-二甲基-4-氯喹啉-1-碘化物 在 二氮杂18-冠醚-6 作用下， 以 正丁醇 为溶剂， 以58.75%的产率得到C₄₂H₄₉N₄O₄⁽¹⁺⁾*I^(1-)
  参考文献：
  名称：

  远红外氮杂-冠醚荧光探针，用于选择性G-四链体DNA靶向

  摘要：

  快速和简单的方法来检测G四联体DNA结构的发展已经引起了广泛的关注，因为它们具有多种生理和病理功能。本研究合成了以氮杂冠醚（TPAQD-ACE）为G4s DNA探针修饰的新型三苯胺喹啉衍生物，并通过核磁共振和质谱法对其进行了表征。为了提高TPAQD-ACE对G4s DNA的选择性，使用了具有不同金属离子（Ni 2 +，Co 2 +，Cu 2 +，Zn 2 +，Fe 3+）的三苯胺喹啉氮杂-冠醚配合物合成名为TPAQD-M-ACE的探针。研究了TPAQD-ACE和TPAQD-M-ACE与G4 DNA相互作用的选择性和结合特性。在中性缓冲液中发出约640 nm信号的TPAQD-Ni-ACE和TPAQD-Fe-ACE具有出色的荧光选择性，不仅可以有效区分G4 DNA与单链和双链DNA，而且还可以分别识别C-myc和Hum45。还通过分子对接详细描述了荧光探针与G4 DNA的结合特性。这些结果表明

  DOI：

  10.1016/j.dyepig.2020.108222
• 作为产物：
  描述：

  苯胺 在 环丁砜 、 alpha-(1-氨基乙基)-苯甲醇 、 三氯氧磷 作用下， 生成 1,2-dimethyl-4-iodo-quinolin-1-ium chloride 、 1,2-二甲基-4-氯喹啉-1-碘化物
  参考文献：
  名称：

  设计，合成和评估2-芳基乙烯基-N-甲基喹啉鎓衍生物作为治疗阿尔茨海默氏病的有效多功能剂。

  摘要：

  根据我们之前对2-芳基乙烯基喹啉类似物作为多功能药物治疗阿尔茨海默氏病（AD）的研究，设计和合成了一系列2-芳基乙烯基-N-甲基喹啉鎓衍生物（Eur.J.Med.Chem.2015，89， 349-361）。体外生物活性评估的结果包括β-淀粉样蛋白（Aβ）聚集抑制，胆碱酯酶抑制和抗氧化活性，表明在喹啉环中引入N-甲基可显着提高化合物的抗AD潜力。最佳化合物a12通过阻止ROS的产生并增加GSH的水平，大大减轻了谷氨酸诱导的HT22细胞的细胞死亡。最重要的是，a12•HAc的胃内给药对高达2000 mg / kg的剂量具有良好的耐受性，并且可以穿越血脑屏障。

  DOI：

  10.1016/j.ejmech.2017.02.042

文献信息

• Discovery of Small Molecules for Up-Regulating the Translation of Antiamyloidogenic Secretase, a Disintegrin and Metalloproteinase 10 (ADAM10), by Binding to the G-Quadruplex-Forming Sequence in the 5′ Untranslated Region (UTR) of Its mRNA
  作者：Jie Dai、Zhen-Quan Liu、Xiao-Qin Wang、Jing Lin、Pei-Fen Yao、Shi-Liang Huang、Tian-Miao Ou、Jia-Heng Tan、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1021/acs.jmedchem.5b00139

  日期：2015.5.14

  Up-regulation of a disintegrin and metalloptoteinase 10 (ADAM10) to prevent the formation of beta-amyloid (A beta) peptides might be a promising strategy to treat Alzheimer's disease (AD). RNA G-quadruplex motif within the 5'-UTR of the ADAM10 mRNA is an inhibitory element for ADAM10 translation. Thus, mitigation of the suppressive effect of this motif using an RNA G-quadruplex-forming G-rich sequence (QGRS) binder might be a new approach for AD therapy. Herein, a series of new methylquinolinium derivatives were synthesized and screened by surface plasmon resonance (SPR) and the dual-luciferase reporter assay. Among them, compound 24 showed selective affinity for the QGRS of ADAM10 and could strongly up-regulate the translation of it. Moreover, treatment with 24 led to a significant increase of the secretion of sAPP alpha, consequently decreasing the A beta(40) in cellular. These results illustrate that the ititeraction between the RNA QGRS and a small molecule may be a new molecular strategy to modulate the translation of ADAM10.
• Facile syntheses of disubstituted bis(vinylquinolinium)benzene derivatives as G-quadruplex DNA binders
  作者：Zhen-Quan Liu、Shi-Tian Zhuo、Jia-Heng Tan、Tian-Miao Ou、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.tet.2013.04.045

  日期：2013.6

  A series of disubstituted bis(vinylquinolinium)benzene derivatives were designed, which were prepared through a facile three-component one-pot reaction in good yield. FRET results showed that 1,3-disubstituted benzene derivatives had much stronger stabilization effect on G-quadruplex DNA than that of 1,4-disubstituted benzene derivatives. The introduction of substituted amine side chain at quinolinium obviously increased the binding affinity of compounds to G-quadruplex DNA. It was also found that 1,3-disubstituted benzene derivatives and 1,4-disubstituted benzene derivatives had different effects on the conformation of G-quadruplex DNA by CD spectroscopy analysis. The differences for the interactions of these two classes of compounds with G-quadruplex were further studied and elaborated through molecular modeling experiments. (C) 2013 Elsevier Ltd. All rights reserved.
• A triphenylamine-based colorimetric and fluorescent probe with donor–bridge–acceptor structure for detection of G-quadruplex DNA
  作者：Ming-Qi Wang、Wen-Xiang Zhu、Zhuan-Zhuan Song、Shuo Li、Yong-Zhao Zhang

  DOI：10.1016/j.bmcl.2015.11.007

  日期：2015.12

  In this Letter, three triphenylamine-based dyes (TPA-1, TPA-2a and TPA-2b) with donor-bridge-acceptor (D-p-A) structure were designed and synthesized for the purpose of G-quadruplexes recognition. In aqueous conditions, the interactions of the dyes with G-quadruplexes were studied with the aim to establish the influence of the geometry of the dyes on their binding and probing properties. Results indicate that TPA-2b displays significant selective colorimetric and fluorescent changes upon binding of G-quadruplex DNA. More importantly, its distinct color change enables visual detection and differentiation of G-quadruplexes from single and duplex DNA structures. CD titration date reveals that TPA-2b could induce and stabilize the formation of G-quadruplex structure. All these remarkable properties of TPA-2b suggest that it should have promising application in the field of G-quadruplexes research. (C) 2015 Elsevier Ltd. All rights reserved.