1,2-dimethylquinolinium 4-methylbenzenesulfonate | 42952-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dimethylquinolinium 4-methylbenzenesulfonate
• 英文别名: 1,2-dimethylquinolinium p-toluenesulfonate；1,2-dimethylquinolin-1-ium 4-methylbenzenesulfonate；1,2-Dimethylquinolinium tosylate；1,2-dimethylquinolin-1-ium;4-methylbenzenesulfonate
• CAS: 42952-26-1
• 化学式: C₇H₇O₃S*C₁₁H₁₂N
• 分子量: 329.42
• InChiKey: FTEJVNFLKLXOLR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dimethylquinolinium 4-methylbenzenesulfonate 在 吡啶 、 三氯氧磷 作用下， 反应 1.25h， 生成 1-methyl-2-(2-chloro-2-trichloromethylvinyl)quinolinium dichlorophosphate
  参考文献：
  名称：

  Chaika, E. A.; Matyushecheva, G. I.; Yagupol'skii, L. M., Journal of Organic Chemistry USSR (English Translation), 1982, p. 165 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基喹啉 、 对甲苯磺酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 以76%的产率得到1,2-dimethylquinolinium 4-methylbenzenesulfonate
  参考文献：
  名称：

  有机 NLO 晶体的合成、生长、晶体结构、热、介电和太赫兹传输特性的研究：(2-(2-羟基-3-甲氧基苯乙烯基) -1-甲基喹啉-4-甲基苯磺酸盐( O - HMQ)

  摘要：

  我们研究了一种适用于太赫兹应用的有机非线性光学 (NLO) 晶体 (2-(2-羟基-3-甲氧基苯乙烯基) -1-甲基喹啉-4-甲基苯磺酸盐( O - HMQ)。本研究阐述了合成、晶体结构, O -HMQ 晶体在太赫兹频率下的热稳定性和介电和传输特性。我们实验室成功合成了O -HMQ。H 1 -NMR 和 FTIR 结果揭示了分子结构。尺寸为 7 × 3 × 的O -HMQ 单晶通过溶剂蒸发技术从甲醇溶液中生长3 mm 3单晶 X 射线衍射数据表明O-HMQ属于单斜晶体结构，空间群为C 2/c。熔点分析显示约 72°C 的相变和中间相。对 1kHz 到 1MHz 的不同频率进行了随温度变化的介电研究，证明了相变。估计介电常数的实部 (ε r ʹ)、虚部 (ε i ″) 和介电损耗 (tanδ)。此外，我们使用 50 fs 超短双色激光等离子体源在 0.1-50 THz 的宽光谱范围内展示了我们生长的O

  DOI：

  10.1016/j.molstruc.2021.131099

文献信息

• Aza-benzazolium containing cyanine dyes
  申请人：Molecular Probes, Inc.

  公开号：US06664047B1

  公开（公告）日：2003-12-16

  Unsymmetrical cyanine dyes that incorporate an aza-benzazolium ring moiety are described, including cyanine dyes substituted by a cationic side chain, monomeric and dimeric cyanine dyes, chemically reactive cyanine dyes, and conjugates of cyanine dyes. The subject dyes are virtually non-fluorescent when diluted in aqueous solution, but exhibit bright fluorescence when associated with nucleic acid polymers such as DNA or RNA, or when associated with detergent-complexed proteins. A variety of applications are described for detection and quantitation of nucleic acids and detergent-complexed proteins in a variety of samples, including solutions, electrophoretic gels, cells, and microorganisms.

  描述了包含aza-苯并唑环部分的非对称花青染料，包括通过阳离子侧链取代的花青染料、单体和多聚花青染料、化学活性花青染料以及花青染料偶联物。主题染料在水溶液中稀释时几乎无荧光，但当与核酸聚合物如DNA或RNA结合，或与洗涤剂-蛋白质复合物结合时，则表现出明亮的荧光。描述了用于检测和定量各种样品中的核酸和洗涤剂-蛋白质复合物的一组应用，包括溶液、电泳凝胶、细胞和微生物。
• Development of Novel Rhodacyanine-Based Heat Shock Protein 70 Inhibitors
  作者：Chih-Shiang Chang、Vathan Kumar、Der-Yen Lee、Yeh Chen、Yu-Chieh Wu、Jing-Yan Gao、Po-Chen Chu

  DOI：10.2174/0929867328666210203204254

  日期：2021.9.8

  A growing body of evidence suggests that Hsp70, which is overexpressed in human breast tumors, plays a role in tumorigenesis and tumor progression in breast cancer as well as in its aggressive phenotypes. Hsp70 constitutes a potential therapeutic target in the treatment of this disease.

  We developed a new series of rhodacyanine-based Hsp70 inhibitors, represented by compounds 1 and 6, in which the cationic pyridin-1-ium or thiazol-3-ium ring of existing Hsp70 inhibitors (e.g., JG-40 and JG-98) was replaced by a corresponding benzo- fused N-heterocycle.

  Several lines of evidence suggest that these benzo-fused derivatives may exert their antitumor activities, in part, by targeting Hsp70. These putative inhibitors displayed differential antiproliferative efficacy against breast cancer cells (IC₅₀ as low as 0.25 μM) versus nontumorigenic MCF-10A breast epithelial cells (IC₅₀ ≥ 5 μM). This was correlated with the corresponding Hsp70 expression levels. Using a protein refolding assay, we confirmed that these agents effectively inhibited the chaperone activity of Hsp70. Moreover, these inhibitors effectively suppressed the expression of well-known oncogenic client proteins of Hsp70’s, including FoxM1, HuR, and Akt, which paralleled their antiproliferative efficacy. Supporting the established role of Hsp70 in regulating protein refolding, these derivatives induced autophagy, as manifested by the conversion of LC3B-I to LC3B-II. Notably, these putative Hsp70 inhibitors did not cause a compensatory elevation in Hsp90 expression, contrasting with the previously reported effects of Hsp90 inhibitors on Hsp70 upregulation.

  Together with the finding that compounds 1 and 6 showed improved microsomal stability, these results suggest the translational potential of these putative Hsp70 inhibitors to foster new strategies for cancer therapy. However, whether these benzo-fused rhodacyanines act on kinases or other targets remains unclear. It is currently under investigation.

  背景：越来越多的证据表明，在人类乳腺肿瘤中过度表达的Hsp70在乳腺癌的肿瘤发生和进展以及其侵袭性表型中发挥作用。Hsp70构成了治疗该疾病的潜在治疗靶点。 方法：我们开发了一系列基于罗达氰基的Hsp70抑制剂，代表物为化合物1和6，其中现有Hsp70抑制剂（例如JG-40和JG-98）的阳离子吡啶-1-ium或噻唑-3-ium环被相应的苯并N-杂环取代。 结果：多条证据表明，这些苯并融合衍生物可能部分通过靶向Hsp70发挥其抗肿瘤活性。这些假定的抑制剂对乳腺癌细胞显示出不同的抗增殖效力（IC50低至0.25μM），而对非肿瘤性MCF-10A乳腺上皮细胞的IC50≥5μM。这与相应的Hsp70表达水平相关。通过蛋白质重折叠实验，我们确认这些药物有效地抑制了Hsp70的分子伴侣活性。此外，这些抑制剂有效地抑制了Hsp70的已知致癌客体蛋白，包括FoxM1、HuR和Akt的表达，这与它们的抗增殖效力相一致。支持Hsp70在调节蛋白质重折叠中的已知作用，这些衍生物诱导了自噬，表现为LC3B-I向LC3B-II的转化。值得注意的是，这些假定的Hsp70抑制剂不会引起Hsp90表达的补偿性升高，与先前报道的Hsp90抑制剂对Hsp70上调的效应形成对比。 结论：与化合物1和6显示出改善的微粒体稳定性的发现一起，这些结果表明这些假定的Hsp70抑制剂在促进癌症治疗新策略方面具有转化潜力。然而，这些苯并融合罗达氰是否作用于激酶或其他靶点仍不清楚，目前正在进行研究。
• Benzodipyrrolenine-based biscyanine dyes: Synthesis, molecular structure and spectroscopic characterization
  作者：Oleksiy P. Klochko、Iryna A. Fedyunyayeva、Sania U. Khabuseva、Olga M. Semenova、Ewald A. Terpetschnig、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2009.09.007

  日期：2010.4

  conventional counterepart, which relies upon condensation of a quaternized benzodipyrrolenine with Fisher's aldehyde, for the synthesis of a symmetrically substituted dyes that contain various heterocyclic end-groups. Investigations of the spectral and luminescent properties of the dyes in solution revealed that the absorption (596–717 nm) and emission (629–773 nm) maxima of the biscyanines were red-shifted

  一种新的长波吸收和发射双三甲胺染料的合成新方法是将苯并二吡咯啉二醛与季铵化的杂环CH-酸性化合物缩合，以制备一系列双花菁。该新方法比常规对等方法更方便，该常规对等方法是将季铵化的苯并二吡咯啉与费舍尔醛缩合，以合成包含各种杂环端基的对称取代的染料。对染料在溶液中的光谱和发光特性的研究表明，与母体“单体”花青相比，双花青素的最大吸收（596–717 nm）和最大发射（629–773 nm）红移了约100 nm。仅包含一种发色的聚次甲基系统。-1  cm -1）和量子产率（≤28％）。两个末端苯并恶唑部分均被吲哚啉，苯并噻唑，2-和4-喹啉取代，使吸收和发射最大值出现红移，但降低了量子产率。
• N-Methylquinolinium derivatives for photonic applications: Enhancement of electron-withdrawing character beyond that of the widely-used N-methylpyridinium
  作者：Jae-Hyeok Jeong、Ji-Soo Kim、Jochen Campo、Seung-Heon Lee、Woo-Yong Jeon、Wim Wenseleers、Mojca Jazbinsek、Hoseop Yun、O-Pil Kwon

  DOI：10.1016/j.dyepig.2014.07.016

  日期：2015.2

  styryl quinolinium push–pull chromophores have been designed and synthesized in order to examine the electron-withdrawing strength of various quinolinium electron acceptor groups, and their influence on the photophysical properties and in particular on the second-order nonlinear optical response. The static molecular first hyperpolarizabilities measured by long-wavelength hyper-Rayleigh scattering are

  为了研究各种喹啉电子受体基团的吸电子强度及其对光物理性质的影响，特别是对二阶非线性光学的影响，设计并合成了一系列π共轭苯乙烯基喹啉鎓推挽生色团。回复。发现通过长波超瑞利散射测量的静态分子第一超极化率遵循由NMR分析确定的其受体基团的吸电子强度的顺序。基于最强电子受体基团（1,2-和1,4-二甲基喹啉鎓）的喹啉鎓发色团显示出非常大的233和256×10 -30的第一超极化率 分别高于著名的和广泛使用的吡啶鎓类似物4-甲基苯磺酸的4-（4-（二甲氨基）苯乙烯基）-1-甲基吡啶鎓4-甲基苯磺酸盐的Esu值，其第一超极化率为183×10 -30  esu。与4-（4-（二甲基氨基）苯乙烯基）-1-甲基吡啶-4-甲基苯磺酸盐中使用的二甲基吡啶基相比，二甲基喹啉鎓电子受体基团表现出更高的吸电子强度，因此在光子应用中具有很高的潜力。
• Heterocyclic compounds containing 4,6-bis-trichloromethyl-s-triazin-2-ly
  申请人：Hoechst Aktiengesellschaft

  公开号：US05055579A1

  公开（公告）日：1991-10-08

  Compounds of general formula I are disclosed ##STR1## wherein L denotes a hydrogen atom, an aryl radial or a substituent of the formula ##STR2## M denotes an alkylene radical or alkenylene radical or a 1,2-arylene radical, Q denotes a sulfur, selenium or oxygen atom, a dialkylmethylene group, an alken 1,2-ylene radical, a 1,2-phenylene radical or an N-R.sup.1 group, denotes an alkyl, aralkyl, aryloxyalkyl or alkoxyalkyl radical, R.sup.2 and R.sup.3 denote a hydrogen atom or a 4,6-bis-trichloromethyl-s-triazin-2-yl group, and n is 0 or 1. The compounds are suitable for use as photoinitiators in photosensitive systems that are induced to reaction by free radicals or acid cations. The compounds are characterized by high sensitivity in the visible spectral region.

  通式I的化合物被揭示，其中L表示氢原子、芳基或公式中的取代基M表示烷基基团或烯基基团或1,2-芳基基团，Q表示硫、硒或氧原子、二烷基亚甲基基团、烯基1,2-亚基基团、1,2-苯基基团或N-R.sup.1基团，表示烷基、芳基、芳氧基烷基或烷氧基烷基基团，R.sup.2和R.sup.3表示氢原子或4,6-双三氯甲基-s-三嗪-2-基团，n为0或1。这些化合物适用于用作光引发剂，用于由自由基或酸阳离子诱导反应的光敏感系统。这些化合物具有在可见光谱区域的高灵敏度。