4-chloro-1-methylquinolinium iodide | 18436-77-6

• 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-chloro-1-methylquinolinium iodide
• 英文别名: N-methyl-4-chloroquinolinium iodide；4-chloro-1-methylquinolin-1-ium;iodide
• CAS: 18436-77-6
• 化学式: C₁₀H₉ClN*I
• 分子量: 305.546
• InChiKey: YNVSUEIOWWNWIE-UHFFFAOYSA-M

物化性质

• 熔点：
  208 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-chloro-1-methylquinolinium iodide 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 N,N'-bis(p-tolylsulfonyl)-1-methylchinolinium-4-sulfinamidinat
  参考文献：
  名称：

  REAKTIONEN VON THIOXOVRBINDUNGEN MIT N-Chloramiden VI.1THIOCHINOLONE, 二氢噻唑硫酮和二氢异噻唑硫酮 MIT N-N-氯苯磺胺

  摘要：

  摘要 研究了 N-氯苯磺酰胺钠 (1a-1e) 与以下杂环 (A) 的 N-烷基硫代二氢衍生物的反应：喹啉、异喹啉、噻唑、异噻唑、苯并噻唑、1,2-苯并异噻唑、2,1-苯并异噻唑, 1,2-苯并异噻唑 1,1-二氧化物。反应产物是 N-芳基磺酰基-S-(二氢杂亚芳基)亚磺酰亚胺(B)、N,N'-双(芳基磺酰基)杂芳基亚磺酰胺(C)和N-(二氢杂亚芳基)芳基磺酰胺(D)。一些磺酰亚胺 (B) 的氧化得到 N-(芳基磺酰基) 杂芳基磺酰胺 (E)。结合 B-E 的情况进行了讨论。Reaktionen von Natrium-N-chlorbenzolsulfonamiden (1a–1e) mit N-Alkylthioxo-dihydroderivaten fogender Heterocyclen (A) 和其他词： Chinolin, Isochinolin, Thiazol, Isothiazol

  DOI：

  10.1080/10426509608029652
• 作为产物：
  描述：

  4-羟基喹啉 在 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 4-chloro-1-methylquinolinium iodide
  参考文献：
  名称：

  Twisted Cyanines: A Non-Planar Fluorogenic Dye with Superior Photostability and its Use in a Protein-Based Fluoromodule

  摘要：

  The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named alpha-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that alpha-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. alpha-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that alpha-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of alpha-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. alpha-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new alpha-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that alpha-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.

  DOI：

  10.1021/ja308629w

文献信息

• New Cyanine–Oligonucleotide Conjugates: Relationships between Chemical Structures and Properties
  作者：Rémy Lartia、Ulysse Asseline

  DOI：10.1002/chem.200500908

  日期：2006.3.1

  range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines, the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5'-end or to an internucleotidic phosphate. In the first

  由于单甲胺花菁-寡核苷酸2'-脱氧核糖核苷酸（ODN）共轭物的化学结构对其结合和荧光性质的影响仍未确定，因此我们合成并研究了多种具有各种结构模式的共轭物。获得了不同的花青染料，例如硫氰酸，喹啉和噻唑橙的异构体。对于不对称花青，连接子连接到喹啉或苯并噻唑核上。ODN对应物的影响通过将花青素连接到5'端或核苷酸间磷酸进行评估。在第一种情况下，研究了相邻核酸碱基的影响，而在第二种情况下，研究了带有花青的磷原子处的立体化学构型。我们在这里报告染料和缀合物的结构及其某些特性之间的关系，例如在与目标序列杂交时观察到的稳定性和荧光变化。这项研究为ODN-花青共轭物的设计提供了有用的信息。
• Quaternary heterocyclylamino .beta.-lactams: a generic alternative to the classical acylamino side chain
  作者：John Hannah、Charles R. Johnson、Arthur F. Wagner、Edward Walton

  DOI：10.1021/jm00346a024

  日期：1982.4

  beta-[(1-substituted-4-pyridinio)amino]ceph-3-em-4-carboxylates have been found to be interesting new classes of antibacterial beta-lactams, readily available by SN2 Ar coupling of fluoro-substituted quaternized pyridines and appropriate amino lactam carboxylic acids. Compared to penicillin G, the penam 12c exhibited a spectrum extended to Gram-negative species, such as Escherichia, Shigella, Klebsiella

  已经发现6个β-[（（1-取代的4-吡啶基）氨基] penam-3-羧酸酯和7个β-[（（1-取代的4-吡啶基）氨基] ceph-3-em-4-羧酸酯有趣的新型抗菌β-内酰胺类，可以通过SN2 Ar偶合氟取代的季铵化吡啶和合适的氨基内酰胺羧酸来获得。与青霉素G相比，penam 12c的光谱扩展到革兰氏阴性菌，如埃希氏菌，志贺氏菌，克雷伯菌和肠杆菌，被针对革兰氏阳性菌的效力丧失所抵消。除假单胞菌外，许多头孢实例均显示出对上述革兰氏阴性生物的优异活性，在某些情况下，例如15i，该光谱包括对葡萄球菌和链球菌的良好表现。由于有沙雷氏菌和许多变形杆菌，
• Antibacterial activity evaluation and mode of action study of novel thiazole-quinolinium derivatives
  作者：Ying Li、Ning Sun、Hooi-Leng Ser、Wei Long、Yanan Li、Cuicui Chen、Boxin Zheng、Xuanhe Huang、Zhihua Liu、Yu-Jing Lu

  DOI：10.1039/d0ra00691b

  日期：——

  active compounds with new mechanisms of action. Based on the molecular structures of the FtsZ inhibitors reported, a variety of thiazole-quinolinium derivatives with aliphatic amino and/or styrene substituents were synthesized from benzothiazolidine derivatives. In the present study, to further explore the antibacterial potential of thiazole-quinolinium derivatives, several Gram-positive and Gram-negative

  迫切需要新的抗菌剂来解决多重耐药生物的出现，特别是那些具有新作用机制的活性化合物。根据报道的 FtsZ 抑制剂的分子结构，从苯并噻唑烷衍生物合成了多种具有脂肪族氨基和/或苯乙烯取代基的噻唑-喹啉衍生物。在本研究中，为了进一步探索噻唑喹啉衍生物的抗菌潜力，用新修饰的化合物处理了几种革兰氏阳性和革兰氏阴性细菌，并详细研究了其生物学效应，以了解其杀菌作用。化合物。我们的研究结果表明，其中一些衍生物具有良好的杀菌活性，因为它们可以抑制革兰氏阳性耐甲氧西林金黄色葡萄球菌、耐万古霉素肠球菌以及一些革兰氏阴性菌和 NDM-1大肠杆菌。此外，化合物4a1-4a4和4b1-4b4改变了细菌细胞的形态，并且与未经处理的细胞相比，这些细胞显示出更细长的形状。生化分析表明，4a4和4b4刺激细菌细胞中的 FtsZ 聚合，最终破坏其动态组装和 Z 环形成。对细菌细胞分裂中这一关键步骤的抑制可能代表了它们抗菌活性的主
• DNA gated photochromism and fluorescent switch in a thiazole orange modified diarylethene
  作者：Keyin Liu、Ying Wen、Ting Shi、Yi Li、Fuyou Li、Yi-lei Zhao、Chunhui Huang、Tao Yi

  DOI：10.1039/c4cc02783c

  日期：——

  Thiazole orange-modified diarylethene (1) shows weak fluorescence but no photochromism in aqueous solution. When binding with DNA, the fluorescence of 1 is enhanced drastically and the photochromic reactivity is unlocked. This kind of DNA-responsive photoswitchable system can be used for imaging nucleic acids within cells.

  噻唑橙修饰的二元蒽（1）在水溶液中会发出微弱的荧光，但没有光致变色作用。当与 DNA 结合时，1 的荧光急剧增强，光致变色反应活性被释放。这种 DNA 响应光开关系统可用于细胞内核酸的成像。
• Single point mutation detection in living cancer cells by far-red emitting PNA–FIT probes
  作者：N. Kolevzon、D. Hashoul、S. Naik、A. Rubinstein、E. Yavin

  DOI：10.1039/c5cc07502e

  日期：——

  SNP detection of the mutated kRAS oncogene in living cells is shown to be achieved for the first time by cell-permeable and far-red emitting PNA–FIT probes.

  在活细胞中首次通过细胞渗透性和远红外发射PNA-FIT探针成功检测到突变的kRAS癌基因的SNP。