2-methyl-3-pentylbenzothiazoliumiodide | 104415-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-methyl-3-pentylbenzothiazoliumiodide
• 英文别名: 2-Methyl-3-pentyl-1,3-benzothiazol-3-ium iodide；2-methyl-3-pentyl-1,3-benzothiazol-3-ium;iodide
• CAS: 104415-36-3
• 化学式: C₁₃H₁₈NS*I
• 分子量: 347.263
• InChiKey: PBYWVIZHMZLUNN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-pentylbenzothiazoliumiodide 在 sodium hydroxide 作用下， 以 水 为溶剂， 以50%的产率得到2-methylene-3-pentyl-2,3-dihydrobenzothiazole
  参考文献：
  名称：

  NLO chromophores containing dihydrobenzothiazolylidene and dihydroquinolinylidene donors with an azo linker: Synthesis and optical properties

  摘要：

  We report the synthesis of a series of nonlinear optical chromophores containing either - a dihydrobenzothiazolylidene or dihydroquinolinylidene donor with an azo linker. The results demonstrate the versatility of coupling a diazonium salt to a donor-methylidene nucleus in order to access novel materials with good thermal stabilities and high nonlinear optical responses. From hyper-Raleigh scattering studies it was found that the use of the well-known TCF acceptor yields the best performing chromophores, one of which has a dynamic first hyperpolarizability of 1900 x 10(-30) esu at 800 nm. The results from this study suggest the use of pro-aromatic donors such as dihydrobenzothiazolylidene or dihydroquinolinylidene results in compounds with higher nonlinear optical responses than those containing donors based on either indoline or aniline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.010
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 1-碘戊烷 以 乙腈 为溶剂， 反应 24.0h， 以59%的产率得到2-methyl-3-pentylbenzothiazoliumiodide
  参考文献：
  名称：

  N-烷基季铵盐典型花青前体的合成和光谱表征

  摘要：

  描述了从苯并噻唑、苯并恶唑、苯并硒唑、吲哚和喹啉衍生的一些代表性 N-烷基取代季铵盐的合成和光谱表征。这些杂环盐在与氮原子和 N-甲基、-戊基、-己基和-癸基链相关的 2-位带有活化的甲基，是花青染料的典型前体。

  DOI：

  10.3390/70300320

文献信息

• Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines
  作者：A. Pardal、S. Ramos、P. Santos、L. Reis、P. Almeida

  DOI：10.3390/70300320

  日期：——

  The synthesis and spectroscopic characterisation of some representative N-alkyl-substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo-selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine

  描述了从苯并噻唑、苯并恶唑、苯并硒唑、吲哚和喹啉衍生的一些代表性 N-烷基取代季铵盐的合成和光谱表征。这些杂环盐在与氮原子和 N-甲基、-戊基、-己基和-癸基链相关的 2-位带有活化的甲基，是花青染料的典型前体。
• Acridinium‐conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation
  作者：Di Song、Nan Zhang、Yangchun Ma、Shenyan Zhang、Weijin Chen、Ting Guo、Shutao Ma

  DOI：10.1002/ardp.202100400

  日期：2022.6

  newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned

  多重耐药性 (MDR) 的流行对公众健康构成严重威胁，迫切需要具有新作用机制的新型抗生素。我们合理设计并高效合成了三个具有潜在抗菌活性的新化学实体，靶向丝状温度敏感突变体 Z (FtsZ)。对这些化合物对一组革兰氏阳性菌（包括耐多药和耐万古霉素肠球菌 菌株）的评估表明，大多数化合物显示出增强的抗菌功效，与参考药物相当甚至更好。新合成的化合物被证明是大肠杆菌的底物外排泵AcrB，从而影响活性。详细总结了它们的构效关系。最有效的化合物10f以杀菌模式快速消除细菌，对诱导细菌耐药性的敏感性较低。对Bs FtsZ 蛋白的进一步机制研究表明，10f通过刺激机制改变 FtsZ 自聚合的动力学，从而起到有效的 FtsZ 抑制剂的作用，从而抑制细胞分裂和细胞死亡。此外，10f不仅对哺乳动物细胞没有明显的细胞毒性，而且在体内菌血症小鼠模型中也具有很高的疗效。作为一个整体，我们的研究结果突出了10f作为一种有前途的新型
• An Insight into Symmetrical Cyanine Dyes as Promising Selective Antiproliferative Agents in Caco-2 Colorectal Cancer Cells
  作者：João L. Serrano、Ana Maia、Adriana O. Santos、Eurico Lima、Lucinda V. Reis、Maria J. Nunes、Renato E. F. Boto、Samuel Silvestre、Paulo Almeida

  DOI：10.3390/molecules27185779

  日期：——

  Several cytotoxic approaches have been used over the years to overcome this public health threat, such as chemotherapy, radiotherapy, and photodynamic therapy (PDT). Cyanine dyes are a class of compounds that have been extensively studied as PDT sensitisers; nevertheless, their antiproliferative potential in the absence of a light source has been scarcely explored. Herein, the synthesis of eighteen symmetric

  癌症仍然是全球发病率最高的疾病之一。多年来，已经使用了几种细胞毒性方法来克服这种公共卫生威胁，例如化学疗法、放射疗法和光动力疗法 (PDT)。花青染料是一类作为PDT增感剂已被广泛研究的化合物；然而，它们在没有光源的情况下的抗增殖潜力几乎没有被探索过。本文描述了 18 种对称单、三和七次甲基花青染料的合成及其作为潜在抗癌剂的评估。分析了杂环性质、抗衡离子和次甲基链长对抗增殖作用和选择性的影响，并收集了相关的构效关系数据。还评估和讨论了光对最有希望的染料的细胞毒活性的影响。研究中的大多数单甲碱和三甲碱花青染料在初始筛选（10 µM ）。然而，浓度-活力曲线显示 Caco-2 细胞系的效力和选择性更高。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示 Caco-2 细胞系具有更高的效力和选择性。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示
• 一种氮杂吩噻嗪化合物及其制备方法
  申请人：五邑大学

  公开号：CN117209508A

  公开（公告）日：2023-12-12

  本发明公开了一种氮杂吩噻嗪化合物及其制备方法，其具有式Ⅰ所示的结构：#imgabs0#R1选自H、卤素、C1～6的烷基；R2选自C1～10的烷基、C1～6的烷氧基、苯基或被任选地选自卤素、C1～10的烷基、C1～6的烷氧基、苯基、氨基取代的苯基；R3选自H、C1～6的烷基、苯基、嘧啶基、噻吩基、取代或未取代地吡啶基；R4选自杂芳基、二茂铁基、苯基或被任选地选自卤素、C1～6的烷基、卤素取代的C1～6的烷基、C1～6的烷氧基、苯基、氨基取代的苯基。本发明提供了一系列氮杂吩噻嗪化合物，该化合物具有药物活性，也可以作为药物中间体合成抗高血压药类似物。
• NMR spectroscopy study of 2-methylbenzoxazolium salts hydroxylation in DMSO-d6 solution
  作者：Ricardo Santos、Luís M. Fernandes、Renato F. Boto、Rogério Simões、Paulo Almeida

  DOI：10.1016/j.tetlet.2006.07.091

  日期：2006.9

  2-Methylbenzoxazolium salts showed an unexpected transformation at room temperature, promoted by residual water present in dimethyl sulfoxide. This transformation was followed up inside of an NMR sample tube using DMSO-d(6) as solvent, in a series of representative quaternary ammonium salts with carboxymethyl, ethyl, pentyl and decyl N-alkyl chains, resulting in an exclusive product. The corresponding benzothiazolium and benzoselenazolium salts presented a si similar behavior after heating at a temperature of 50 degrees C with the addition of one drop of D2O for the first of these two salts. This reaction could play a very important role in explaining certain secondary reactions occurring in the preparation of compounds where these salts are precursors, classically in cyanine dye synthesis. Four new benzoxazolols were characterized by NMR spectroscopy and HR FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.