(Z)-3-甲基-2-(2-(N-苯基乙酰氨基)乙烯基)苯并[d]噻唑-3-碘化物 | 62196-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (Z)-3-甲基-2-(2-(N-苯基乙酰氨基)乙烯基)苯并[d]噻唑-3-碘化物
• 英文名称: 2-[2-(N-acetyl-anilino)-vinyl]-3-methyl-benzothiazolium; iodide
• 英文别名: N-[(Z)-2-(3-methyl-1,3-benzothiazol-3-ium-2-yl)ethenyl]-N-phenylacetamide;iodide
• CAS: 62196-30-9
• 化学式: C₁₈H₁₇N₂OS*I
• 分子量: 436.316
• InChiKey: BOYYVBYNBOANGD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-甲基-2-(2-(N-苯基乙酰氨基)乙烯基)苯并[d]噻唑-3-碘化物 在 氨 作用下， 以 乙醇 为溶剂， 生成 1,5-bis-(3-methyl-benzothiazol-2-yl)-3-aza-pentamethinium; iodide
  参考文献：
  名称：

  Mukherjee,K. et al., Journal of the Indian Chemical Society, 1970, vol. 47, p. 1121 - 1128

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯并噻唑 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (Z)-3-甲基-2-(2-(N-苯基乙酰氨基)乙烯基)苯并[d]噻唑-3-碘化物
  参考文献：
  名称：

  A comparative study of symmetrical and unsymmetrical trimethine cyanine dyes bearing benzoxazolyl and benzothiazolyl groups

  摘要：

  Six symmetrical and unsymmetrical trimethine cyanine dyes bearing benzothiazolyl and benzoxazolyl groups were synthesized. Their linear optical properties were studied. It was found that the variation of hetero atoms play an important role in the spectral properties of the dyes. Sequential replacement of the oxygen atom by the sulfur atom resulted in a change in shade from yellow to purple. In order to understand the relationship between the molecular structures and the spectral properties of these dyes, theoretical calculations were made using the Gaussian programme. Key parameters related to absorption and emission spectra were reported and discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.11.001

文献信息

• Hybridization-sensitive fluorescence control in the near-infrared wavelength range
  作者：Shuji Ikeda、Hiroyuki Yanagisawa、Akiko Nakamura、Dan Ohtan Wang、Mizue Yuki、Akimitsu Okamoto

  DOI：10.1039/c1ob05252g

  日期：——

  A series of near-infrared fluorescent probes were designed based on the concept of emission control caused by interdye excitonic interaction. The fluorescent probes showed very weak emission in the unhybridized state, whereas they emitted near-infrared fluorescence after hybridization with the complementary nucleic acid. The hybridization-dependent switching of fluorescence emission made it possible to monitor mRNA in human cells in the range of near-infrared wavelengths.

  一系列近红外荧光探针是基于染料间激发子相互作用导致的发射控制概念设计的。这些荧光探针在未杂交状态下发射非常微弱的荧光，而在与互补核酸杂交后则发出近红外荧光。荧光发射的杂交依赖性开关使得在近红外波长范围内监测人类细胞中的mRNA成为可能。
• D-π-A-π-D Dyes with a 1,3,2-Dioxaborine Cycle in the Polymethine Chain: Efficient Long-Wavelength Fluorophores
  作者：Vladyslav Polishchuk、Mariia Stanko、Andrii Kulinich、Mykola Shandura

  DOI：10.1002/ejoc.201701466

  日期：2018.1.17

  nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4-(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value

  新合成的 5-cyano-2,2-difluoro-4,6-dimethyl-1,3,2-dioxaborine 中的腈基显示出显着增加甲基的酸度。这使得花青与两个甲基基团缩合形成 D–π–A–π–D 染料，其中二恶硼啉循环是聚甲炔链的一部分。在那里，半产物中剩余甲基的反应性降低到足以逐步进行反应，从而获得非对称衍生物。报告了具有各种电子供体末端 [吲哚、苯并噻唑、吡喃、4-(二烷基氨基)苯基] 和具有不同聚次甲基链长的染料的合成。所得化合物在红色和近红外区域显示出强烈的吸收和荧光，它们的荧光亮度（摩尔消光和荧光量子产率的乘积）达到 200,000 m–1 cm–1 的值。它们的特点是小规模的正溶剂化变色，但它们的荧光量子产率对环境极性更敏感。已经进行了时间相关 (TD)DFT 计算来研究新二氧杂环戊二烯的电子结构并揭示这些分子中长波长电子跃迁的性质。
• [EN] PHOTOTOXIC COMPOUNDS<br/>[FR] COMPOSES PHOTOTOXIQUES
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2005123105A1

  公开（公告）日：2005-12-29

  The invention discloses various phototoxic compounds which include a photosensitizer conjugated to a peptide or peptoid. Additionally, the invention discloses a method of making and using the various phototoxic compound. Furthermore, the invention discloses using such phototoxic compound for DNA cleavage and for causing cytotoxic effect in a biological system. Additionally, the present invention features using the phototoxic compound for treating diseases in a subject.

  本发明公开了多种光毒性化合物，其中包括与肽或peptoid共轭的光敏剂。此外，本发明还公开了一种制备和使用各种光毒性化合物的方法。此外，本发明还公开了使用这种光毒性化合物进行DNA断裂和在生物系统中引起细胞毒性效应的方法。此外，本发明还特别涉及使用这种光毒性化合物治疗主体中的疾病。
• Key Structural Elements of Unsymmetrical Cyanine Dyes for Highly Sensitive Fluorescence Turn-On DNA Probes
  作者：Kakishi Uno、Taeko Sasaki、Nagisa Sugimoto、Hideto Ito、Taishi Nishihara、Shinya Hagihara、Tetsuya Higashiyama、Narie Sasaki、Yoshikatsu Sato、Kenichiro Itami

  DOI：10.1002/asia.201601430

  日期：2017.1.17

  a series of unsymmetrical cyanine dyes plays a critical role in the fluorescence enhancement. Four newly designed unsymmetrical cyanine dyes showed negligible intrinsic fluorescence in the free state and strong fluorescence upon binding to double‐stranded DNA (dsDNA) with a quantum yield of 0.53 to 0.90, which is 2 to 3 times higher than previous unsymmetrical cyanine dyes. A detailed analysis of the

  非对称花青染料（例如噻唑橙）可用于检测具有荧光的核酸，因为它们在结合核酸后会显着增强荧光。在这里，我们合成了一系列不对称的花青染料，并评估了它们的荧光特性。一项系统的结构-性质关系研究表明，一系列不对称花青染料中喹啉2位的二烷基氨基在荧光增强中起关键作用。四种新设计的不对称花青染料在游离状态下显示可忽略的固有荧光，与双链DNA（dsDNA）结合后显示强荧光，其量子产率为0.53至0.90，这是以前的不对称花青染料的2至3倍。荧光寿命的详细分析表明，喹啉2位的二烷基氨基抑制了非辐射衰变，从而增加了荧光量子产率。此外，这些新开发的染料能够通过共聚焦激光扫描显微镜对固定的HeLa细胞中的细胞核进行特殊染色。
• 381. Cyanine dyes from 2 : 3-dihydro-β-quinindene
  作者：A. B. Lal、V. Petrow

  DOI：10.1039/jr9480001895

  日期：——