3-(2-carboxyethyl)-2-methylbenzo thiazol-3-ium iodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(2-carboxyethyl)-2-methylbenzo thiazol-3-ium iodide
• 英文别名: N-(2-carboxyethyl)-2-methylbenzothiazolium iodide；3-(2-Carboxyethyl)-2-methylbenzo[d]thiazol-3-ium iodide；3-(2-methyl-1,3-benzothiazol-3-ium-3-yl)propanoic acid;iodide
• 化学式: C₁₁H₁₂NO₂S*I
• 分子量: 349.192
• InChiKey: MUHFRIOWLDIZBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.02
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-carboxyethyl)-2-methylbenzo thiazol-3-ium iodide 、 对二甲氨基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以79%的产率得到N-(2-carboxyethyl)-2-[4-(N,N-dimethylamino)styryl]benzothiazolium iodide
  参考文献：
  名称：

  The N-(2-carboxyethyl)hemicyanine dyes. Synthesis, properties and quantum-chemical calculations

  摘要：

  Three new hernicyanine dyes possessing donor-pi-acceptor structure that features a fixed p-substituted phenyl ring as an electron donor and benzothiazolium moiety as an electron acceptor were synthesized. The structure of dyes was elucidated by using NMR and IR spectroscopy and elemental analysis. The spectroscopic properties have been investigated by spectroscopic experiments and time-dependent density functional theory (TD-DFT) calculations at the B3LYP/6-311++G(d,p) level of theory. The measurements and calculations were performed in five different polarity solvents. The strong absorption of all dyes in the range from 450 to 600 nm is observed. The relationship between electronic absorption spectra of hemicyanine dyes and their molecular structure is also discussed. The molecular structure does not have large change during the intramolecular charge-transfer (ICT) process, which is confirmed by the quantum chemical calculations. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2014.12.019
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 3-碘丙酸 以 乙腈 为溶剂， 反应 30.0h， 以66%的产率得到3-(2-carboxyethyl)-2-methylbenzo thiazol-3-ium iodide
  参考文献：
  名称：

  新型 N-(羧乙基)-2-甲基苯并噻唑基半花青染料：合成、光谱、光稳定性和与牛血清白蛋白的结合

  摘要：

  三种含有N-(羧乙基)-2-甲基苯并噻唑鎓基团并在苯乙烯基部分的苯环的对位上带有不同取代基的半花青染料很容易通过Knoevenagel缩合制备。研究了它们的紫外/可见光和荧光光谱、聚集、光稳定性以及与牛血清白蛋白的关联。染料在不同溶剂中的最大吸收和发射波长在 520-620 nm 范围内。与典型的 N-烷基-2-甲基苯并噻唑鎓半菁染料相比，羧乙基基团的引入减少了聚集并提高了摩尔消光系数，以及在水中的光稳定性。这些染料可以预见它们在光动力疗法中的潜在用途。还描述了所有合成染料的光谱表征。

  DOI：

  10.1016/j.molstruc.2014.12.032

文献信息

• [EN] MOLECULAR SENSOR AND METHODS OF USE THEREOF<br/>[FR] CAPTEUR MOLÉCULAIRE ET SES PROCÉDÉS D'UTILISATION
  申请人：YEDA RES & DEV

  公开号：WO2014102803A1

  公开（公告）日：2014-07-03

  The present invention is directed to fluorescent molecular sensor based on thiazole orange as represented below for protein detection. Interaction of the protein target with the molecular sensors of this invention results in a significant increase in the fluorescence emission. The generation of light output signal enables one to detect protein biomarkers associated with different diseases or detecting the protein of interest also in living cells.

  本发明涉及一种基于噻唑橙的荧光分子传感器，用于蛋白质检测。本发明的分子传感器与蛋白质靶标的相互作用导致荧光发射显著增加。光输出信号的产生使得可以检测与不同疾病相关的蛋白生物标志物，或者在活细胞中检测感兴趣的蛋白质。
• [EN] CANCER CELL INHIBITORY DRUG AND CANCER STEM-CELL DETECTION PROBE<br/>[FR] MÉDICAMENT INHIBITEUR DE CELLULES CANCÉREUSES ET SONDE DE DÉTECTION DE CELLULES SOUCHES CANCÉREUSES
  申请人：CANON KK

  公开号：WO2014065440A1

  公开（公告）日：2014-05-01

  An object of the present invention is to provide a cancer cell inhibitory drug, particularly a cancer stem-cell inhibitory drug, or a cancer stem-cell detection probe.A cancer cell inhibitory drug containing at least a compound represented by general formula (1).

  本发明的目的是提供一种抗癌药物，特别是一种抗癌干细胞的药物，或一种癌干细胞检测探针。一种抗癌细胞的药物，其中至少包含一个由通式（1）表示的化合物。
• MOLECULAR SENSOR AND METHODS OF USE THEREOF
  申请人：YEDA RESEARCH AND DEVELOPMENT CO. LTD.

  公开号：US20150276753A1

  公开（公告）日：2015-10-01

  The present invention is directed to fluorescent molecular sensor based on Thiazole Orange for protein detection. Interaction of the protein target with the molecular sensors of this invention results in a significant increase in the fluorescence emission. The generation of light output signal enables one to detect protein biomarkers associated with different diseases or detecting the protein of interest also in living cells.

  本发明涉及一种基于Thiazole Orange的荧光分子传感器，用于蛋白质检测。本发明的分子传感器与蛋白质靶标的相互作用导致荧光发射显著增加。光输出信号的产生使得人们能够检测与不同疾病相关的蛋白质生物标志物或者在活细胞中检测感兴趣的蛋白质。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Fe: Org.Verb.A5, 5.1.5.12, page 64 - 88
  作者：

  DOI：——

  日期：——
• Ferrocene dyes and photographic elements
  申请人：EASTMAN KODAK COMPANY

  公开号：US03577238A1

  公开（公告）日：1971-05-04