(5-benzo[c,d]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5-benzo[c,d]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-(Benz[cd]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-(1H-benzo[cd]indol-2-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: LPGVUKBMBXBDNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-benzo[c,d]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.33h， 生成 N-Methyl-2-methylbenzindolium-iodid
  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 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 (5-benzo[c,d]indol-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  用于精确癌症光治疗的线粒体靶向 NIR-II 分子荧光团

  摘要：

  亚细胞器线粒体正在成为癌症的关键参与者和驱动因素。线粒体靶向光治疗在精准癌症治疗方面引起了越来越多的关注。然而，这些光治疗系统仍然面临着巨大的挑战，包括组件复杂、多、光散射、治疗效果不足等。在此，通过分子工程巧妙地设计了分子荧光团 IR-TPP-1100，用于第二近红外窗口（NIR-II）中的线粒体靶向荧光成像引导光疗。 IR-TPP-1100不仅表现出突出的光物理性质和高光热转换效率，而且还实现了优异的线粒体靶向能力。靶向线粒体的 IR-TPP-1100 能够在生物体水平上对线粒体进行 NIR-II 荧光和光声双模态成像。此外，它还整合了光热和光动力疗法，通过诱导线粒体凋亡获得了显着的肿瘤治疗效果。这些结果表明 IR-TPP-1100 在精准癌症治疗方面具有巨大潜力，并为开发靶向线粒体的 NIR-II 光治疗剂提供了一种有前途的策略。

  DOI：

  10.1021/acs.jmedchem.3c01677

文献信息

• 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）。
• Photochromic properties of cationic merocyanine dyes. Thermal stability of the spiropyran form produced by irradiation with visible light
  作者：Shigeyuki Yagi、Katsumi Maeda、Hiroyuki Nakazumi

  DOI：10.1039/a905098a

  日期：——

  A series of novel cationic merocyanine dyes were prepared by condensation of 1,2,3,3-tetramethylindolium derivatives and 3-formyl-4H-1-benzothiopyran or -benzopyran derivatives, and their photochromic properties were investigated, especially focusing on the substituent effect in the indolium moiety. These dyes were converted into the spiropyran (SP) form so as to be colorless by irradiation with visible light, although, left under darkness, the colored merocyanine (MC) form was reproduced. The thermal coloration was affected by two factors: the substituent in the indolium moiety and the counter anion. An electron-donating substituent such as a methoxy group at the 5 position effectively retarded the thermal coloration, whereas an electron-withdrawing group such as a nitro group accelerated it. These substituent effects afforded good linearity for the Hammett rule with para σ parameters, indicating that decrease of the electron density in the indoline moiety of the SP form facilitated heterolytic cleavage of the bond between the spiro carbon and the oxygen of the pyran ring.

  通过缩合反应制备了一系列新型阳离子型部花青染料，该反应涉及1,2,3,3-四甲基吲哚鎓衍生物与3-醛基-4H-1-苯并噻吡喃或苯并吡喃衍生物的反应，并研究了它们的光致变色性质，特别关注吲哚鎓部分中的取代基效应。这些染料在可见光照射下转化为无色的螺吡喃（SP）形式，尽管在黑暗环境中，带色的部花青（MC）形式会再次出现。热致变色受到两个因素的影响：吲哚鎓部分的取代基和反荷离子。在5位带有供电子取代基（如甲氧基）有效地延缓了热致变色，而吸电子基团（如硝基）则加速了热致变色。这些取代基效应提供了良好的Hammett规则线性关系，对应于para σ参数，表明在SP形式中吲哚部分电子密度降低促进了螺碳与吡喃环氧之间键的异裂解离。
• CYANINE-CONTAINING COMPOUNDS FOR CANCER IMAGING AND TREATMENT
  申请人：Emory University

  公开号：US20150335765A1

  公开（公告）日：2015-11-26

  This invention relates generally to cyanine-containing compounds; pharmaceutical compositions comprising cyanine-containing compounds; and methods of using cyanine-containing compounds for cancer cell imaging, cancer cell growth inhibition, and detecting cancer cells, for example. Compounds of the invention are preferentially taken up by cancer cells as compared to normal cells. This allows many uses in the cancer treatment, diagnosis, tracking and imaging fields.

  这项发明通常涉及含有青霉素的化合物；包含青霉素化合物的药物组合物；以及使用青霉素化合物进行癌细胞成像、癌细胞生长抑制和检测癌细胞等方法。该发明的化合物相对于正常细胞更容易被癌细胞吸收。这使得在癌症治疗、诊断、跟踪和成像领域有许多用途。
• [EN] NEAR INFRARED ABSORBING FLUORESCENT COMPOSITIONS<br/>[FR] COMPOSITIONS FLUORESCENTES ABSORBANT DANS L'INFRAROUGE PROCHE
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2016025620A1

  公开（公告）日：2016-02-18

  Provided herein are heterocyclic near infrared compounds, including near IR compounds defined by Formulae I-V described herein. The near infrared compounds can include a cyanine group, a phthalocyanine group, a naphthalocyanine group, a squaraine group, a carbocyanine group, or a combination thereof. In some embodiments, the near infrared compound can be charged. In some embodiments, the near infrared compound can comprise a cationic group. Compositions comprising the near infrared compounds are also disclosed. In some embodiments, the composition can contain the near infrared compound, a polymer, and an acceptable carrier. In some embodiments, the polymer can include an anionic group. The compositions can be used as a coating for marking a surface, such as an ink. The compositions can also be used on articles for detecting, identifying, or authenticating the article. Methods of making the compositions described herein are also disclosed.

  本文提供了杂环近红外化合物，包括根据本文所描述的式I-V定义的近红外化合物。这些近红外化合物可以包括青菁基团、酞菁基团、萘酞菁基团、方酰胺基团、碳基青菁基团或其组合。在某些实施方式中，近红外化合物可以带电。在某些实施方式中，近红外化合物可以包含阳离子基团。还披露了含有这些近红外化合物的组合物。在某些实施方式中，该组合物可以包含近红外化合物、聚合物和可接受的载体。在某些实施方式中，聚合物可以包含阴离子基团。这些组合物可以用作涂层，用于标记表面，例如墨水。这些组合物还可以用于检测、识别或认证物品。还披露了制备本文描述的组合物的方法。
• Near infrared absorbing fluorescent compositions
  申请人：GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.

  公开号：US10377901B2

  公开（公告）日：2019-08-13

  Provided herein are heterocyclic near infrared compounds, including near IR compounds defined by Formulae I-V described herein. The near infrared compounds can include a cyanine group, a phthalocyanine group, a naphthalocyanine group, a squaraine group, a carbocyanine group, or a combination thereof. In some embodiments, the near infrared compound can be charged. In some embodiments, the near infrared compound can comprise a cationic group. Compositions comprising the near infrared compounds are also disclosed. In some embodiments, the composition can contain the near infrared compound, a polymer, and an acceptable carrier. In some embodiments, the polymer can include an anionic group. The compositions can be used as a coating for marking a surface, such as an ink. The compositions can also be used on articles for detecting, identifying, or authenticating the article. Methods of making the compositions described herein are also disclosed.

  本文提供的是杂环近红外化合物，包括本文所述式 I-V 所定义的近红外化合物。近红外化合物可包括氰基、酞菁基、萘酞菁基、鳞烷基、羰基或它们的组合。在某些实施例中，近红外化合物可以带电。在某些实施例中，近红外化合物可以包含阳离子基团。还公开了包含近红外化合物的组合物。在某些实施例中，组合物可以包含近红外化合物、聚合物和可接受的载体。在某些实施方案中，聚合物可以包括阴离子基团。组合物可用作标记表面的涂层，如墨水。组合物还可用于物品上，以检测、识别或鉴定物品。本文还公开了制造所述组合物的方法。