2-[3-bromo-5-(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-3H-indolium iodide | 68979-06-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[3-bromo-5-(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-3H-indolium iodide
• 英文别名: indodicarbo-μ-(bromo) cyanine iodide；1,5-bis-(1-ethyl-3,3-dimethyl-3H-indol-2-yl)-3-bromo pentamethinium ; iodide；1,5-Bis-(1-aethyl-3,3-dimethyl-3H-indol-2-yl)-3-brom-pentamethinium; Jodid；2-[3-bromo-5-(1-ethyl-3,3-dimethylindol-1-ium-2-yl)penta-2,4-dienylidene]-1-ethyl-3,3-dimethylindole;iodide
• CAS: 68979-06-6
• 化学式: C₂₉H₃₄BrN₂*I
• 分子量: 617.411
• InChiKey: FXLAVZDPEWMXSG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-[3-bromo-5-(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-3H-indolium iodide 在 C₂₀H₂₈Cl₂N₅O₂Pd 、 4-氯苯硼酸 、 potassium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 反应 1.0h， 以30%的产率得到2-[5-(1-ethyl-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene)-1,3-pentadienyl]-1-ethyl-3,3-dimethyl-3H-indolium iodide
  参考文献：
  名称：

  New acyclic Pd–diaminocarbene catalyst for Suzuki arylation of meso-chlorosubstituted tricarboindocyanine dyes

  摘要：

  Acyclic Pd-diaminocarbene complex showed high catalytic activity in Suzuki arylation of meso-chlorine-substituted tricarboindocyanine dyes. Arylated dyes were obtained in 57-83% yields in the presence of 5 x 10(-4) equiv of catalyst. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.060
• 作为产物：
  描述：

  1-乙基-2,3,3-三甲基吲哚鎓碘化物 、 N-[2-bromo-3-(phenylamino)-2-propenylidene]-benzenammonium bromide 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以57%的产率得到2-[3-bromo-5-(1-ethyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-3H-indolium iodide
  参考文献：
  名称：

  前所未有的酸催化内消旋-溴吲哚并二羰花青染料的Wurtz型偶合

  摘要：

  在酸催化下，内消旋-溴取代的茚并二羰花青染料与脱溴物质一起生成二聚体分子。二聚化和加氢脱溴途径之间的关系取决于染料的芳基取代。还提出了可能的反应机理。

  DOI：

  10.1016/j.tetlet.2017.07.043

文献信息

• Symmetric, monofunctionalised polymethine dyes labelling reagents
  申请人：Innosense S.r.l.

  公开号：EP1221465A1

  公开（公告）日：2002-07-10

  A symmetric cyanine of the formula: wherein: X is selected from the group consisting of O, S and C(CH3)2; W represents non-metal atoms required to form a benzo-condensed or a naphto-condensed ring; R1 is selected from the group consisting of (CH2)nCH3, (CH2)nSO3- and (CH2)nSO3H, wherein n is an integer selected from 0 to 6 when R1 is (CH2)nCH3, and n is an integer selected from 3 to 6 when R1 is (CH2)nSO3- or (CH2)nSO3H; R2 and R3 are independently selected from the group consisting of H, a sulphonic moiety and a sulphonate moiety; Q is selected from the group consisting of: wherein q is 0 or 1 and D is selected from the group consisting of:         -C≡C-G; and wherein A is O or S and G is, or contains a N, O or S nucleophile moiety or is, or contains a moiety capable of reacting with N, O or S nucleophiles.

  公式为：其中：X从O、S和C(CH3)2组成的组中选择；W代表形成苯并或萘并环所需的非金属原子；R1从(CH2)n 、( )nSO3-和( )nSO3H组成的组中选择，其中当R1为( )n 时，n是从0到6选择的整数，当R1为( )nSO3-或( )nSO3H时，n是从3到6选择的整数；R2和R3独立地从H、磺酸基团和磺酸盐基团组成的组中选择；Q从以下组成的组中选择：其中q为0或1，D从以下组成的组中选择：-C≡C-G；其中A为O或S，G是或含有N、O或S亲核基团，或是或含有能与N、O或S亲核基团发生反应的基团。
• An Approach to Developing Cyanines with Simultaneous Intersystem Crossing Enhancement and Excited-State Lifetime Elongation for Photodynamic Antitumor Metastasis
  作者：Xueze Zhao、Qichao Yao、Saran Long、Weijie Chi、Yuxin Yang、Davin Tan、Xiaogang Liu、Haiqiao Huang、Wen Sun、Jianjun Du、Jiangli Fan、Xiaojun Peng

  DOI：10.1021/jacs.1c06275

  日期：2021.8.11

  electron-rich moieties at the meso position of the pentamethine cyanine (Cy5) skeleton, which simultaneously enhanced intersystem crossing (ISC) and prolonged excited-state lifetime. We found that the 1O2 generation ability is directly correlated to the electron-donating ability of the meso substituent in cyanine, and the excited-state lifetime was simultaneously much elongated when the substituents were

  基于重原子的光敏剂通常表现出缩短的三重态寿命，这对于缺氧肿瘤光动力治疗并不理想。尽管几种不含重原子的光敏剂具有较长的三重态寿命，但其临床适用性受限于它们的短激发波长、较差的光子捕获能力和固有的疏水结构。在这里，我们开发了一种新的近红外无重原子光敏剂设计策略，通过在五次甲基花青 (Cy5) 骨架的中间位置引入空间庞大和富含电子的部分，同时增强系统间交叉 (ISC) 和延长激发态寿命. 我们发现1 O 2生成能力与花青中的中间取代基的给电子能力直接相关，当取代基为9位取代的蒽衍生物时，激发态寿命同时大大延长。我们的明星化合物 ANOMe-Cy5 表现出强烈的近红外吸收，最高的1 O 2量子产率（比 Cy5 高 4.48 倍）、最长的三重态寿命（比 Cy5 长 9.80 倍）和无损发射强度（与 Cy5 相比几乎没有变化）。这种优异的光物理特性加上其固有的阳离子和亲水性，使光敏剂能够实现实体瘤的光
• 一类单光子上转换五甲川菁类光敏染料、其制备方法和应用
  申请人：大连理工大学

  公开号：CN114045045B

  公开（公告）日：2022-11-04

  本发明提供一类单光子上转换五甲川菁类光敏染料、其制备方法和应用，所述光敏染料具有通式I的结构。本发明所述无重原子修饰的、具有单光子上转换性质的五甲川菁类光敏染料，拥有在长于自身最大吸收波长处的光激发下高的单线态氧产生能力。在上转换光的激发下能够对深层组织下的癌细胞进行有效地光动力杀伤，并可用于活体内实体肿瘤的光动力治疗，对抑制深层肿瘤生长有良好的应用前景。
• Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake
  作者：Eric A. Owens、Hoon Hyun、Joseph G. Tawney、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.5b00475

  日期：2015.5.28

  Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical, properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the,delineation of delicate glands.
• Jezewski et al., Roczniki Chemii, 1956, vol. 30, p. 467,470, 473
  作者：Jezewski et al.

  DOI：——

  日期：——