1-butyl-2-methylbenzo[cd]indol-1-ium iodide | 1151666-46-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-butyl-2-methylbenzo[cd]indol-1-ium iodide
• 英文别名: 1-Butyl-2-methylbenzo[cd]indol-1-ium;iodide
• CAS: 1151666-46-4
• 化学式: C₁₆H₁₈N*I
• 分子量: 351.23
• InChiKey: KZAFOXGAGPBPLT-UHFFFAOYSA-M

物化性质

• 熔点：
  >300 °C(Solv: ethanol (64-17-5); water (7732-18-5))

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-butyl-2-methylbenzo[cd]indol-1-ium iodide 在 乙酸酐 、 三氯氧磷 作用下， 反应 0.5h， 生成 5-bromo-2-((1E,3E)-3-(1-butylbenzo[c,d]indol-2(1H)-ylidene)prop-1-en-1-yl )-3,3-dimethyl-1-(3-(trimethylammonio)propyl)-3H-indol-1-ium dibromide
  参考文献：
  名称：

  Second Generation G-Quadruplex Stabilizing Trimethine Cyanines

  摘要：

  G-四链 DNA 被认为是开发新型选择性化疗药物的一个非常吸引人的靶点，这可能显著减少对正常细胞的毒性。特别是，选择性结合 G-四链结构而不针对双链 DNA 的氰染料因其高度适应结构改造而受到关注，这使得对其生物分子相互作用进行微调成为可能。我们之前报道了设计用于通过末端堆叠相互作用有效结合 G-四链的五甲基和对称三甲基氰染料。在这里，我们报告了一种第二代药物候选物，即不对称三甲基氰染料。这些化合物已经合成并评估了它们的四链结合属性。引入苯[c,d]吲哚啉杂环单元提高了整体四链结合能力，而延长烷基链的长度则增加了四链与双链的结合特异性。

  DOI：

  10.1021/acs.bioconjchem.9b00571
• 作为产物：
  描述：

  1,8-萘内酰亚胺 在 吡啶 、 tetraphosphorus decasulfide 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.33h， 生成 1-butyl-2-methylbenzo[cd]indol-1-ium iodide
  参考文献：
  名称：

  Second Generation G-Quadruplex Stabilizing Trimethine Cyanines

  摘要：

  G-四链 DNA 被认为是开发新型选择性化疗药物的一个非常吸引人的靶点，这可能显著减少对正常细胞的毒性。特别是，选择性结合 G-四链结构而不针对双链 DNA 的氰染料因其高度适应结构改造而受到关注，这使得对其生物分子相互作用进行微调成为可能。我们之前报道了设计用于通过末端堆叠相互作用有效结合 G-四链的五甲基和对称三甲基氰染料。在这里，我们报告了一种第二代药物候选物，即不对称三甲基氰染料。这些化合物已经合成并评估了它们的四链结合属性。引入苯[c,d]吲哚啉杂环单元提高了整体四链结合能力，而延长烷基链的长度则增加了四链与双链的结合特异性。

  DOI：

  10.1021/acs.bioconjchem.9b00571

文献信息

• Synthesis and effect of heterocycle modification on the spectroscopic properties of a series of unsymmetrical trimethine cyanine dyes
  作者：Andrew Levitz、Safieh Tork Ladani、Donald Hamelberg、Maged Henary

  DOI：10.1016/j.dyepig.2014.02.009

  日期：2014.6

  quantum yield and molar absorptivity. The aggregation of these cyanine dyes was studied and compared to a similar series of symmetric cyanine dyes. It was determined that the heterocycle has more effect on aggregation than the side chain and a dye with two different heterocycles will aggregate less than a dye with the same heterocycle. The dyes were also investigated for Lipinski Rule violations as their

  碳菁染料是一类有机化合物，其中包含两个杂环，这些杂环充当通过共轭次甲基桥连接的电子供体和受体。本文报道了一系列16种新型不对称三甲胺花青染料的合成。通过各种光谱技术表征了它们的结构，并测量了它们的光学性质。使用随时间变化的密度泛函理论方法计算染料的吸收最大值，并且计算的吸收最大值与实验数据一致。在杂环上添加吸电子取代基例如卤素给出了更有利的光学性质，例如更高的量子产率和摩尔吸收率。对这些花青染料的聚集进行了研究，并将其与类似系列的对称花青染料进行了比较。已确定杂环比侧链对聚集的影响更大，并且具有两个不同杂环的染料的聚集将比具有相同杂环的染料的聚集少。还研究了这种染料是否违反Lipinski规则，因为它们的使用越来越普遍。体内应用。
• Functionalization of benzo[<i>c,d</i>]indole system for the synthesis of visible and near-infrared dyes
  作者：Maged Henary、Mariusz Mojzych、Martial Say、Lucjan Strekowski

  DOI：10.1002/jhet.39

  日期：2009.1

  A number of benzo[c,d]indolium derivatives have been synthesized. J. Heterocyclic Chem., 46, 84 (2009).

  已经合成了许多苯并[ c，d ]吲哚衍生物。杂环化学杂志，46，84（2009）。
• Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
  作者：Sarmistha Halder Sinha、Eric A. Owens、You Feng、Yutao Yang、Yan Xie、Yaping Tu、Maged Henary、Yujun George Zheng

  DOI：10.1016/j.ejmech.2012.06.017

  日期：2012.8

  Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Influence of Solid-State Packing of Dipolar Merocyanine Dyes on Transistor and Solar Cell Performances
  作者：Alhama Arjona-Esteban、Julian Krumrain、Andreas Liess、Matthias Stolte、Lizhen Huang、David Schmidt、Vladimir Stepanenko、Marcel Gsänger、Dirk Hertel、Klaus Meerholz、Frank Würthner

  DOI：10.1021/jacs.5b06722

  日期：2015.10.28

  A series of nine dipolar merocyanine dyes has been studied as organic semiconductors in transistors and solar cells. These dyes exhibited single-crystal packing motifs with different dimensional ordering, which can be correlated to the performance of the studied devices. Hereby, the long-range ordering of the dyes in staircase-like slipped stacks with J-type excitonic coupling favors charge transport and improves solar cell performance. The different morphologies of transistor thin films and solar cell active layers were investigated by UV-vis, AFM, and XRD experiments. Selenium-containing donor-acceptor (D-A) dimethine dye 4 showed the highest hole mobility of 0.08 cm(2) V-1 s(-1). BHJ solar cells based on dye 4 were optimized by taking advantage of the high crystallinity of the donor material and afforded a PCE of up to 6.2%.
• Second Generation G-Quadruplex Stabilizing Trimethine Cyanines
  作者：Eric A. Owens、Hang T. Huynh、Ekaterina M. Stroeva、Arghya Barman、Kostiantyn Ziabrev、Ananya Paul、Sarah V. Nguyen、Matthew Laramie、Donald Hamelberg、Markus W. Germann、W. David Wilson、Maged Henary

  DOI：10.1021/acs.bioconjchem.9b00571

  日期：2019.10.16

  G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.

  G-四链 DNA 被认为是开发新型选择性化疗药物的一个非常吸引人的靶点，这可能显著减少对正常细胞的毒性。特别是，选择性结合 G-四链结构而不针对双链 DNA 的氰染料因其高度适应结构改造而受到关注，这使得对其生物分子相互作用进行微调成为可能。我们之前报道了设计用于通过末端堆叠相互作用有效结合 G-四链的五甲基和对称三甲基氰染料。在这里，我们报告了一种第二代药物候选物，即不对称三甲基氰染料。这些化合物已经合成并评估了它们的四链结合属性。引入苯[c,d]吲哚啉杂环单元提高了整体四链结合能力，而延长烷基链的长度则增加了四链与双链的结合特异性。