1-octyl-2,3,3-trimethylindoleninium iodide | 96359-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-octyl-2,3,3-trimethylindoleninium iodide
• 英文别名: 1-octyl-2,3,3-trimethyl-3H-indol-1-ium iodide；2,3,3-trimethyl-1-octyl-3H-indol-1-ium iodide；N-octyl-2,3,3-trimethylindoleninium iodide；2,3,3-trimethyl-1-octyl-3H-indolenium iodide；2,3,3-trimethyl-1-octyl-3H-indolium; iodide；1,1,2-trimethyl-3-octylbenzindoline iodide；1-octyl-2,3,3-trimethyl-3H-indolium iodide；2,3,3-Trimethyl-1-octyl-3H-indol-1-ium iodide；2,3,3-trimethyl-1-octylindol-1-ium;iodide
• CAS: 96359-59-0
• 化学式: C₁₉H₃₀N*I
• 分子量: 399.358
• InChiKey: MBWGRQOOHLKDQN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-octyl-2,3,3-trimethylindoleninium iodide 在 三乙胺 作用下， 以 正丁醇 、 苯 为溶剂， 反应 19.0h， 生成 2-[(3,3-Dimethyl-1-octylindol-2-ylidene)methyl]-4-[(3-octyl-1,3-benzothiazol-3-ium-2-yl)methylidene]-3-oxocyclobuten-1-olate
  参考文献：
  名称：

  Synthesis, photophysical study and BSA association of water-insoluble squaraine dyes

  摘要：

  In this work, the synthesis, spectroscopic characterisation, photophysical study and bovine serum albumin association of water-insoluble squaraine dyes are described. The photophysical behaviour of the dyes was investigated using UV-vis and steady-state fluorescence in solution, as well as its association with bovine serum albumin in phosphate buffer solution. No squaraine aggregation was observed in organic solvents, but J-type aggregation could be observed in phosphate buffer solution. In the absence of protein, the J-aggregation promoted the fluorescence quenching; however, upon addition of protein, the fluorescence intensity increased by a factor of up to 80. Additionally, a linear relationship between the fluorescence intensity and the protein concentration could be observed for the squaraine dyes in a concentration range around 0.02-0.10 mu M. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.11.013
• 作为产物：
  描述：

  1-octyl-2,3,3-trimethyl-3H-indol-1-ium bromide 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以40%的产率得到1-octyl-2,3,3-trimethylindoleninium iodide
  参考文献：
  名称：

  N-Alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles. Potential lead compounds in the fight against Saccharomyces cerevisiae infections

  摘要：

  The synthesis of a variety of N-alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles is reported herein. Their potential as antifungal agents is evaluated by preliminary screening against Saccharomyces cerevisiae (S. cerevisiae), Schizosaccharomyces pombe (S. pombe), and Candida albicans (C albicans). Statistical analyses illustrate a strong relationship between chain length and growth inhibition for S. cerevisiae and S. pombe (p < 0.0001 in every case).Of particular interest is the activity of both sets of compounds against S. cerevisiae, as this is emerging as an opportunistic pathogen, especially in immunosuppressed and immunocompromised patients. Bioassays were set up to compare the efficacy of our range of N-alkylated compounds against classic antifungal agents; Amphotericin B and Thiabendazole. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.031

文献信息

• Survey, fluorescence spectra, and solubility of liquid cyanine dyes
  作者：Masaki Matsui、Takaya Yamamoto、Yasuhiro Kubota、Kazumasa Funabiki

  DOI：10.1039/c6nj02160c

  日期：——

  synthesized four liquid cyanine dyes, namely N,N′-didodecyl 44,N,N′-dioctadecyl indolenium 45,N,N′-bis(2,5,8-trioxa-10-octadecanyl)benzoxazolium 50 and benzothiazolium 51, which have a bis(perfluorobutylsulfonyl)imide anion. In the neat form, these liquid dyes exhibit more intense fluorescence at −196 °C than at 25 °C. The liquid N,N′-dialkylated indolenium derivatives 44 and 45 exhibited larger solubility

  我们合成了四种液体花青染料，分别是N，N'-二十二烷基44，N，N'-二十八烷基吲哚45，N，N'-双（2,5,8-三恶唑-10-十八烷基）苯并恶唑50和苯并噻唑鎓51，其具有双（全氟丁基磺酰基）酰亚胺阴离子。以纯净的形式，这些液体染料在-196°C处比在25°C下表现出更强的荧光。液态的N，N'-二烷基化的吲哚衍生物44和45在己烷中的溶解度大于相应的固态衍生物。另外，液态氮，N′-双（2,5,8-三氧杂-10-十八烷基）苯并恶唑鎓和苯并噻唑鎓衍生物50和51比相应的固体衍生物更易溶于丙醇。
• Synthesis, spectroscopic characterization and photophysical study of dicyanomethylene-substituted squaraine dyes
  作者：Diego dos Santos Pisoni、Cesar Liberato Petzhold、Marluza Pereira de Abreu、Fabiano Severo Rodembusch、Leandra Franciscato Campo

  DOI：10.1016/j.crci.2012.01.009

  日期：2012.5

  Résumé In this work, the synthesis and the photophysical study of novel symmetrical and unsymmetrical squaraine dyes is described. These dyes were prepared by base-catalyzed condensation reaction between 3H-indolium or benzothiazolium salts with dicyanomethylene squarate, derived from squaric acid. The photophysical behavior of the dyes was investigated using UV–Vis absorption and steady-state fluorescence in solution. Additionally, its association with albumin from bovine serum (bovine serum albumin [BSA]) was also investigated. The dyes present strong absorption in the red/infrared regions and fluorescence emission in the infrared region tailored by the electronic structure of the squaraine. Association experiments with bovine serum albumin indicate that the obtained squaraine dyes are suitable for protein detection in solution. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  总结 在这项工作中，描述了新型对称和非对称方形染料的合成及其光物理研究。这些染料是通过3H-吲哚鎓盐或苯并噻唑鎓盐与来自方酸的二氰基亚甲基方盐之间的碱催化缩合反应制备的。通过UV-Vis吸收和稳态荧光研究了这些染料的光物理行为。此外，还研究了其与牛血清白蛋白（牛血清白蛋白[BSA]）的结合。染料在红/红外区域表现出强吸收，并在红外区域发射荧光，发射特性受方形染料的电子结构调控。与牛血清白蛋白的结合实验表明，获得的方形染料适合于溶液中蛋白质的检测。 补充材料： 本文的补充材料作为单独文件提供：mmc1.doc
• 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
• Novel Near-Infrared Squaraine Sensitizers for Stable and Efficient Dye-Sensitized Solar Cells
  作者：Chuanjiang Qin、Youhei Numata、Shufang Zhang、Xudong Yang、Ashraful Islam、Kun Zhang、Han Chen、Liyuan Han

  DOI：10.1002/adfm.201303769

  日期：2014.5

  energetically efficient electron injection and regeneration of the oxidized dye. A solar cell sensitized with HSQ4 exhibits a broad incident photo­n‐to‐current conversion efficiency spectrum, extending into the near‐infrared region with a maximum value of 80% at 720 nm, which is is the highest value reported for a squaraine dye–based dye‐sensitized solar cell. The HSQ4‐sensitized solar cell also exhibits

  调节顺式能级的新分子设计策略介绍了用于染料敏化太阳能电池的，配置好的方酸敏化剂。Hammett取代基常数和π共轭长度用作定量指示剂，以修饰敏化染料的中央方形部分；具体而言，新型近红外方酸染料HSQ3和HSQ4是通过在中央方酸部分上结合吸电子和π延伸的氰基乙酸乙酯单元而合成的。HSQ4的溶液吸收最大值出现在703 nm，并且最低未占据分子轨道和最高占据分子轨道的能级在能量有效电子注入和氧化染料再生的理想范围内。用HSQ4敏化的太阳能电池具有宽广的入射光子-电流转换效率谱，延伸到近红外区域，在720 nm处的最大值为80％，这是基于方酸染料的染料敏化太阳能电池的最高报告值。HSQ4敏化的太阳能电池在光浸泡过程中也表现出出色的耐久性，这是由于双锚将染料附着在TiO上2表面和到长的烷基链从表面向外延伸。
• Near‐Infrared Squaraine Dyes as Bright Fluorescent Probes: A Structure–Activity Photophysical Investigation in Liposomes
  作者：Giacomo Renno、Francesca Cardano、Viktoria Ilieva、Guido Viscardi、Andrea Fin

  DOI：10.1002/ejoc.202200833

  日期：2022.10.7

  unsymmetrical red emitting squaraine dyes is reported, varying the substituents to modulate the hydrophilic/hydrophobic ratio of the fluorescent probes. Their ability to stain cellular membranes is assessed by studying their interactions with liposomal model systems, screening the key features for the design of squaraine-based cell membrane probes.

  报道了一个小型对称和不对称红色发射方酸染料库的有效制备，通过改变取代基来调节荧光探针的亲水/疏水比。通过研究它们与脂质体模型系统的相互作用来评估它们对细胞膜染色的能力，筛选基于方酸的细胞膜探针设计的关键特征。