3-(2-benzothiazolyl)-7-hydroxy-2-iminocoumarin | 135008-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(2-benzothiazolyl)-7-hydroxy-2-iminocoumarin
• 英文别名: 3-(1,3-Benzothiazol-2-yl)-2-iminochromen-7-ol
• CAS: 135008-56-9
• 化学式: C₁₆H₁₀N₂O₂S
• 分子量: 294.334
• InChiKey: XMXFOTVFQVMGGZ-UHFFFAOYSA-N

物化性质

• 熔点：
  285-286 °C
• 沸点：
  501.8±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-benzothiazolyl)-7-hydroxy-2-iminocoumarin 在 三氟化硼乙醚 、 三乙胺 作用下， 反应 3.0h， 以95%的产率得到C₁₆H₉BF₂N₂O₂S
  参考文献：
  名称：

  基于3-（杂芳基）-2-亚氨基香豆素的新型硼酸盐配合物：合成，光物理性质和用于生物传感/生物标记应用的合理功能化

  摘要：

  一系列具有酚羟基（用作荧光中心）和N-芳基取代基（用作稳定基团）的3-（杂芳基）-2-亚氨基香豆素配体的一系列二氟化硼配合物的成员通过应用简单的两步法即可获得收益。这些新颖的荧光染料属于“ Boricos”家族（D. Frath等人，Chem。Commun。2013，49，4908-4910），并且其中在绿-黄色光谱范围内的光物理性质正在显着改善由基于苯酚的荧光团的例子第一Ñ，Ñ硼原子的螯合。通过相应的2,4-二硝基苯基（DNP）醚的制备证明了通过可逆的苯酚部分化学修饰来调节其荧光性质，这在与硫醇反应时导致了剧烈的“ OFF-ON”荧光反应。另外，为了扩大这些“ 7-羟基-硼酸”衍生物的范围，特别是在生物标记中，适合于（生物）结合的胺或羧酸官能团已被引入其支架中。它们的用途已在制备荧光牛血清白蛋白（BSA）偶联物和“ Borico” -DOTA样支架中得到证明，以设计新颖的单分子多峰荧光放射性同位素显像剂。

  DOI：

  10.1002/chem.201502126
• 作为产物：
  描述：

  2-氨基苯硫醇 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-(2-benzothiazolyl)-7-hydroxy-2-iminocoumarin
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676

文献信息

• Synthesis and Biological Evaluations of 3-Benzothiazol-2-yl Coumarin Derivatives as MEK1 Inhibitors
  作者：Chao Wang、Fengrong Xu、Yan Niu、Yun Wu、Jing Sun、Yihong Peng、Lei Liang、Ping Xu

  DOI：10.2174/15701808113109990012

  日期：2013.8.1

  In order to discover novel MEK inhibitors, a series of 3-(benzothiazol-2-yl) coumarin derivatives have been synthesized following our earlier study of 3-benzyl coumarin derivatives. The target compounds were obtained by condensation, cyanation, hydrolyzation and esterification starting from o-hydroxy benzaldehydes and benzothiazole-2- acetonitrile. The cyanation reaction could only occur when there were electron with drawing groups at C3 position of coumarin scaffold. All the synthesized compounds showed weak binding and inhibition potencies to phosphorylated MEK1 but obvious inhibitory effect to unphosphorylated MEK1, suggesting that compounds inhibition to MEK1 is mainly due to the inhibition of npMEK1 rather than pMEK1. The most potent compound 3 was with an inhibition rate of 60.7% at 1 μM in the RAF-MEK cascading assay. Molecular docking studies revealed that the pocket occupation and structure hydrophobicity may be important for activity. These results can contribute to further optimization on coumarin scaffold and led to the design of novel coumarin derivatives as more potent MEK1 inhibitors.

  为了发现新型MEK抑制剂，一系列3-(苯并噻唑-2-基)香豆素衍生物被研究 根据我们早期对 3-苄基香豆素衍生物的研究合成的。经缩合得到目标化合物， 以邻羟基苯甲醛和苯并噻唑-2-为原料进行氰化、水解和酯化 乙腈。氰化反应只有在香豆素C3位有带拉基的电子时才能发生 脚手架。所有合成的化合物均对磷酸化 MEK1 表现出较弱的结合和抑制能力 但对未磷酸化的MEK1有明显的抑制作用，提示化合物对MEK1的抑制主要是由于 抑制 npMEK1 而不是 pMEK1。最有效的化合物 3 在 1 μM 时抑制率为 60.7% 在 RAF-MEK 级联测定中。分子对接研究表明口袋占据和结构疏水性 可能对活动很重要。这些结果有助于进一步优化香豆素支架和LED 设计新型香豆素衍生物作为更有效的 MEK1 抑制剂。
• Benzazole Substituted Iminocoumarins as Potential Antioxidants with Antiproliferative Activity
  作者：Nataša Perin、Maja Cindrić、Peter Vervaeke、Sandra Liekens、Tomislav Mašek、Kristina Starčević、Marijana Hranjec

  DOI：10.2174/1573406416666191218101427

  日期：2020.12.29

  which include a wide range of versatile biological activities as well as excellent spectroscopic characteristics thus offering their potential application in many research fields. Objective: The prepared iminocoumarins were synthesized to evaluate their antioxidative potential by using ABTS and FRAP assays and in vitro antiproliferative activity.

  背景：苯并唑和香豆素衍生物是药物化学中最优先的杂环亚结构之一，具有众所周知的生物学特征，其中包括广泛的多种生物活性以及出色的光谱特性，因此在许多研究领域中都具有潜在的应用前景。 目的：合成的亚氨基香豆素通过ABTS和FRAP试验评估其抗氧化能力，并具有体外抗增殖活性。
• ——
  作者：O. V. Khilya、M. S. Frasinyuk、A. V. Turov、V. P. Khilya

  DOI：10.1023/a:1012704121345

  日期：——
• A novel colorimetric and fluorescent probe for the highly selective and sensitive detection of palladium based on Pd(0) mediated reaction
  作者：Kai Wang、Guoqiao Lai、Zhifang Li、Mengmeng Liu、Yongjia Shen、Chengyun Wang

  DOI：10.1016/j.tet.2015.08.021

  日期：2015.10

  In view of palladium contaminants and their adverse effects on human health, it is valuable to develop an effective probe for palladium. In this work, a coumarin-based colorimetric and turn-on fluorescent probe, Cou-1, for highly selective and sensitive detection of palladium was designed based on the Tsuji-Trost allylic reaction. Upon the addition of palladium to the solution of probe, the probe gave an emission peak at around 498 nm as well as displayed a selective chromogenic behavior toward palladium from colorless to yellow-green, which could be easily observed by the naked eye. Moreover, compared with typical transition metal canons and other common cations used, Cou-1 showed great selectivity toward palladium. Further, the detection limit toward palladium was calculated to be as low as 17.4 nM. (c) 2015 Elsevier Ltd. All rights reserved.
• Dual signaling of hypochlorous acid by desulfurization of thiocoumarin
  作者：Jung Ok Moon、Jung Woo Lee、Myung Gil Choi、Sangdoo Ahn、Suk-Kyu Chang

  DOI：10.1016/j.tetlet.2012.09.110

  日期：2012.11

  The HOD-selective signaling behavior of thiocoumarin was investigated. The thio derivative of ethoxycoumarin showed selective and efficient colorimetric and fluorogenic signaling behaviors over other commonly used oxidants in an aqueous environment. The signaling is due to the oxidative desulfurization of the thiocarbonyl moiety by HOCl to yield oxocarbonyl function. The interference from Hg2+ ions was successfully removed by using bromide ions as a masking agent. HOCl signaling with a detection limit of 8.3 x 10(-7) M in the presence of common metal ions and anions as background was possible. The designed probe could be useful for the determination of hypochlorous acid in chemical and environmental samples. (C) 2012 Elsevier Ltd. All rights reserved.