N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]benzamide | 945036-87-3

• 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: N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]benzamide
• 英文别名: N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]-benzamide；N-[(2Z)-2-(1,3,3-trimethylindol-2-ylidene)ethanethioyl]benzamide
• CAS: 945036-87-3
• 化学式: C₂₀H₂₀N₂OS
• 分子量: 336.458
• InChiKey: SFJAMWKUPWYBIA-LGMDPLHJSA-N

物化性质

• 熔点：
  108-110 °C(Solv: methanol (67-56-1))
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]benzamide 在 sodium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以40%的产率得到(Z)-1,3,3-trimethyl-2-cyanomethyleneindoline
  参考文献：
  名称：

  Merocyanine Dyes with Improved Photostability

  摘要：

  Merocyanine dyes have proven valuable for live cell fluorescence imaging applications, but many structures have been limited by rapid photobleaching. We show that photostability is substantially enhanced for merocyanines having a cyano group at a specific position in the central polymethine chain. Evidence is presented that this is due to reduction in reactivity of the dyes with singlet oxygen. These results point toward cyano-substitution as a general strategy for improving dye performance in imaging applications.

  DOI：

  10.1021/ol070780h
• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 、 sodium thiocyanide 、 苯甲酰氯 以 丙酮 为溶剂， 反应 1.0h， 以57%的产率得到N-[(2Z)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)ethanethioyl]benzamide
  参考文献：
  名称：

  Merocyanine Dyes with Improved Photostability

  摘要：

  Merocyanine dyes have proven valuable for live cell fluorescence imaging applications, but many structures have been limited by rapid photobleaching. We show that photostability is substantially enhanced for merocyanines having a cyano group at a specific position in the central polymethine chain. Evidence is presented that this is due to reduction in reactivity of the dyes with singlet oxygen. These results point toward cyano-substitution as a general strategy for improving dye performance in imaging applications.

  DOI：

  10.1021/ol070780h

文献信息

• METHODS TO INCREASE THE PHOTOSTABILITY OF DYES
  申请人：Hahn Klaus

  公开号：US20110046000A1

  公开（公告）日：2011-02-24

  The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live-cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.

  所述主题提供了具有改善光稳定性的染料、包括此类染料的生物传感器以及其使用方法，包括用于检测样品中的靶分子和用于活细胞成像的方法。该染料可以包括结合成员，包括生物分子或其片段，其可以与感兴趣的靶分子相互作用，并且可以特定于给定的构象状态或靶分子的共价修饰，例如磷酸化。目前披露的染料可用于检测靶分子的结合、构象变化或后翻译修饰的变化。
• Methods to increase the photostability of dyes
  申请人：Hahn Klaus

  公开号：US08835632B2

  公开（公告）日：2014-09-16

  The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live-cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.

  目前公开的主题提供了具有改进光稳定性的染料，包括含有这种染料的生物传感器和使用它们的方法，包括检测样品中的目标分子和进行活细胞成像的方法。这些染料可以包括结合成员，包括生物分子或其片段，可以与感兴趣的目标分子相互作用，并且可以特异于给定的构象状态或目标分子的共价修饰，例如磷酸化。目前公开的染料可用于检测目标分子的结合、构象变化或翻译后修饰的变化。
• [EN] METHODS TO INCREASE THE PHOTOSTABILITY OF DYES<br/>[FR] PROCÉDÉS POUR ACCROÎTRE LA PHOTOSTABILITÉ
  申请人：UNIV NORTH CAROLINA

  公开号：WO2008157762A8

  公开（公告）日：2009-03-19
• US8835632B2
  申请人：——

  公开号：US8835632B2

  公开（公告）日：2014-09-16
• [EN] METHODS TO INCREASE THE PHOTOSTABILITY<br/>[FR] PROCÉDÉS POUR ACCROÎTRE LA PHOTOSTABILITÉ
  申请人：UNIV NORTH CAROLINA

  公开号：WO2008157762A2

  公开（公告）日：2008-12-24

  (EN) The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live- cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.(FR) La présente invention concerne des colorants qui présentent une meilleure photostabilité, des biocapteurs comprenant ces colorants et des procédés d'utilisation de ces derniers, y compris des procédés de détection de molécules cibles dans un échantillon soumis à un essai et pour l'imagerie de cellules vivantes. Les colorants peuvent comprendre un élément de liaison renfermant une biomolécule ou un fragment de cette dernière, qui peut interagir avec des molécules cibles présentant un intérêt et qui peuvent être spécifiques d'un état conformationnel donné ou d'une modification covalente donnée, par exemple, la phosphorylation, de la molécule cible. Les colorants selon la présente invention peuvent être utilisés pour détecter des changements concernant la liaison, le changement conformationnel ou la modification post-traduction de la molécule cible.