(Z)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one

• 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: (Z)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one
• 英文别名: (Z)-3-((2-oxoindolin-3-ylidene)amino)-2-thioxothiazolidin-4-one；(5Z)-3-amino-5-(2-oxo-1H-indol-3-ylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• 化学式: C₁₁H₇N₃O₂S₂
• 分子量: 277.327
• InChiKey: DLPCTQRNDPBUEU-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.43
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one 、 四丁基醋酸铵 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  新的N-取代的5-oxindoline-rhodanines的简单合成及其感测能力：水溶液中乙酸根离子的识别†

  摘要：

  最近，人们对开发新颖的罗丹宁芯装饰合成策略越来越感兴趣。此外，从含水有机溶剂介质中检测阴离子引起了人们的极大兴趣，这是在大多数环境和生物系统中普遍观察到的。为此，通过简便有效的合成方法合成了含有重要芳香族基团的新的N-取代的5-氧代吲哚-若丹宁衍生物，并通过比色和荧光检测以及1 H-NMR光谱对其阴离子感测性能进行了评估。该研究显示，对于ACO特定离子亲和-在AQUA系统离子和ACO多离子亲和-，BNO-，CN - ，和F -在导致剧烈的颜色和光谱变化的有机溶剂。根据获得的数据，虽然峰强度在386 nm处增加，但在5-OxI-Rh的吸收光谱中在253 nm处峰强度降低，并且在存在下观察到5-OxI-Rh的荧光强度增加。ACO的-离子。的结合比率5- OXI -铑到ACO -被认为是1：根据作业的情节实验1。的结合常数使用Benesi-希尔德布兰德公式计算，结果为6.51×10 3中号-1为ACO

  DOI：

  10.1039/c9nj01732a
• 作为产物：
  描述：

  N-氨基绕丹宁 、 靛红 以 乙醇 为溶剂， 以72%的产率得到(Z)-3-amino-5-(2-oxoindolin-3-ylidene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  新的N-取代的5-oxindoline-rhodanines的简单合成及其感测能力：水溶液中乙酸根离子的识别†

  摘要：

  最近，人们对开发新颖的罗丹宁芯装饰合成策略越来越感兴趣。此外，从含水有机溶剂介质中检测阴离子引起了人们的极大兴趣，这是在大多数环境和生物系统中普遍观察到的。为此，通过简便有效的合成方法合成了含有重要芳香族基团的新的N-取代的5-氧代吲哚-若丹宁衍生物，并通过比色和荧光检测以及1 H-NMR光谱对其阴离子感测性能进行了评估。该研究显示，对于ACO特定离子亲和-在AQUA系统离子和ACO多离子亲和-，BNO-，CN - ，和F -在导致剧烈的颜色和光谱变化的有机溶剂。根据获得的数据，虽然峰强度在386 nm处增加，但在5-OxI-Rh的吸收光谱中在253 nm处峰强度降低，并且在存在下观察到5-OxI-Rh的荧光强度增加。ACO的-离子。的结合比率5- OXI -铑到ACO -被认为是1：根据作业的情节实验1。的结合常数使用Benesi-希尔德布兰德公式计算，结果为6.51×10 3中号-1为ACO

  DOI：

  10.1039/c9nj01732a

文献信息

• Synthesis and evaluation of new isatin-aminorhodanine hybrids as PIM1 and CLK1 kinase inhibitors
  作者：Khadidja Khaldoun、Abdelmounaim Safer、Nourdine Boukabcha、Necmi Dege、Sandrine Ruchaud、Mohamed Souab、Stéphane Bach、Abdelkader Chouaih、Salima Saidi-Besbes

  DOI：10.1016/j.molstruc.2019.04.122

  日期：2019.9

  A series of new hybrid isatin-aminorhodanine molecules was prepared by microwave activation under mild conditions. Unexpected condensation of isatin derivatives at C-5 position of aminorhodanine was highlighted and confirmed by NMR and X-ray analyses. The inhibitory activity of these compounds was evaluated towards eight protein kinases, CDK's-2,-5,-9; PIM-1, CLK-1, Haspin, GSK3 beta and DYRK1A, whose signaling pathway dysregulation is associated to multifactorial diseases such as cancer, inflammatory, cardiovascular, and neurodegenerative diseases. Compound 3l bearing a bromo substituent has shown a potent and selective Pim1 kinase inhibitor activity. (C) 2019 Elsevier B.V. All rights reserved.
• A simple rhodanine-based fluorescent sensor for mercury and copper: The recognition of Hg2+ in aqueous solution, and Hg2+/Cu2+ in organic solvent
  作者：Sinan Bayindir

  DOI：10.1016/j.jphotochem.2018.12.021

  日期：2019.3

  Detection of copper and mercury attracts important in most environmental and biological systems. In this study, the simple probe 2-OxI-Rh containing rhodanine core was synthesized by a green approach and sensing properties were studied using colorimetric and fluorometric detection. The research indicated that the specific ion affinity for Hg2+ ions in aqua systems and the multi-ion affinity for Hg2+ and Cu2+ in organic solvent results in drastic color and spectral changes. According to the data obtained, while the peak intensity increases at 390 nm, the peak intensity decreased at 272 nm in the absorption spectrum of 2-OxI-Rh and an increase in fluorescence intensity of 2-OxI-Rh were observed in the presence of Hg2+ and Cu2+ ions. The binding ratio of 2-OxI-Rh to Hg2+ and Cu2+ were found to be 1:1 according to Job's plot experiments. The binding constants were calculated using the Benesi-Hildebrand equation and found to be 2.15 x 10(4) M-1 for Hg2+ and 1.21 x 10(4) M-1 for Cu2+. Based on these concentration dependent fluorescence changes, the limit of detection (LOD) values were also calculated and found to be 3.36 mu M for Hg2+ and 2.31 mu M for Cu2+, which is the range of copper that should be in the blood (11.8-23.6 mu M). As a result of all these studies, we can understand that prove 2-OxI-Rh, which is non-toxic, is a good selective candidate turn-on sensor that can be used for Hg2+ and Cu2+ detection in different solvent systems.