2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole | 6265-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole
• 英文别名: HMBT；2-(benzo[d]thiazol-2-yl)-6-methoxyphenol；Phenol, 2-(2-benzothiazolyl)-6-methoxy-；2-(1,3-benzothiazol-2-yl)-6-methoxyphenol
• CAS: 6265-93-6
• 化学式: C₁₄H₁₁NO₂S
• mdl: MFCD01707775
• 分子量: 257.313
• InChiKey: CKFLKUKQCSXXBI-UHFFFAOYSA-N

物化性质

• 沸点：
  431.2±55.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80.4%的产率得到2-(2',3'-dihydroxyphenyl)benzothiazole
  参考文献：
  名称：

  Product-boosted fluorescence signal: a new approach for designing small-molecule probes for detection of peroxynitrite

  摘要：

  利用商业可获得的2-甲醛基苯硼酸和2-(2′,3′-双羟基苯基)苯并噻唑（BHBT）自组装成的硼酸酯，用于检测ONOO-并通过产物增强荧光。

  DOI：

  10.1039/d0cc02963g
• 作为产物：
  描述：

  2-(2-benzoyloxy-3-methoxyphenyl)benzothiazole 在 human carboxylesterase 1 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.33h， 生成 2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole
  参考文献：
  名称：

  Assessment of the inhibitory effects of pyrethroids against human carboxylesterases

  摘要：

  Pyrethroids are broad-spectrum insecticides that widely used in many countries, while humans may be exposed to these toxins by drinking or eating pesticide-contaminated foods. This study aimed to investigate the inhibitory effects of six commonly used pyrethroids against two major human carboxylesterases (CES) including CES1 and CES2. Three optical probe substrates for CES1 (DME, BMBT and DMCB) and a fluorescent probe substrate for CES2 (DDAB) were used to characterize the inhibitory effects of these pyrethroids. The results demonstrated that most of the tested pyrethroids showed moderate to weak inhibitory effects against both CES1 and CES2, but deltamethrin displayed strong inhibition towards CES1. The IC50 values of deltamethrin against CES1-mediated BMBT, DME, and DMCB hydrolysis were determined as 1.58 mu M, 2.39 mu M, and 33 mu M, respectively. Moreover, deltamethrin was cell membrane permeable and capable of inhibition endogenous CES1 in living cells. Further investigation revealed that deltamethrin inhibited CES1-mediated BMBT hydrolysis via competitive manner but noncompetitively inhibited DME or DMCB hydrolysis. The inhibition behaviors of deltamethrin against CES1 were also studied by molecular docking simulation. The results demonstrated that CES1 had at least two different ligand-binding sites, one was the DME site and another was the BMBT site which was identical to the binding site of deltamethrin. In summary, deltamethrin was a strong reversible inhibitor against CES1 and it could tightly bind on CES1 at the same ligand-binding site as BMBT. These findings are helpful for the deep understanding of the interactions between xenobiotics and CES1. (C) 2017 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.taap.2017.02.018
• 作为试剂：
  描述：

  2-氨基苯硫醇 、 邻香草醛 、 双氧水 、 盐酸 在 2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole 、 水 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以to afford the desired product as a light yellow solid (0.64 g, 79% yield)的产率得到2-(2'-hydroxy-3'-methoxyphenyl)benzothiazole
  参考文献：
  名称：

  Fluorescence detection of cysteine and homocysteine

  摘要：

  本发明公开了用于选择性检测具有巯基和氨基的化合物（例如半胱氨酸和/或同型半胱氨酸）的探针实施例，以及用于在中性介质中检测这些化合物的方法和试剂盒。探针具有通用公式所示的结构，其中R1-R4独立地是氢、羟基、卤素、巯基、硫醚、低级脂肪基或低级烷氧基，x是0到4的整数，每个R5独立地是卤素、羟基、巯基、硫醚、低级脂肪基或低级烷氧基。所公开的探针实施例能够与半胱氨酸和/或同型半胱氨酸经历缩合/环化反应。通过确定探针在特征波长处的荧光发射，可以选择性地检测和鉴定半胱氨酸和/或同型半胱氨酸。

  公开号：

  US09229007B2

文献信息

• A new fluorescent ‘turn on’ probe for rapid detection of biothiols
  作者：Muhammed Üçüncü、Hüseyin Zeybek、Erman Karakuş、Canan Üçüncü、Mustafa Emrullahoğlu

  DOI：10.1080/10610278.2021.1893321

  日期：2020.12.1

  ABSTRACT We designed and synthesised a novel molecular probe exhibiting high selectivity and sensitivity towards reactive sulphur species (RSS) over other amino acids and biologically relevant species, as well as scrutinised its spectroscopic behaviours under physiological conditions and in living milieu. We used an electrophilic cyanate group as a masking agent to block the excited state intramolecular

  摘要 我们设计并合成了一种新型分子探针，该探针对其他氨基酸和生物学相关物种具有很高的选择性和对活性硫物种（RSS）的敏感性，并仔细研究了其在生理条件下和生活环境中的光谱行为。我们使用亲电子的氰酸酯基作为掩蔽剂来阻止2-（2-氰基-3-甲氧基苯基）苯并[d]噻唑（HMBT-OCN）的激发态分子内质子转移过程，该过程易于水解为高荧光结构，在反应性硫原子的存在下，生成2-（2ʹ-羟基-3ʹ-甲氧基苯基）苯并噻唑（HMBT-OH）。
• IMMUNOSUPPRESSIVE COMPOUNDS
  申请人：Mesaik Muhammad A.

  公开号：US20140378515A1

  公开（公告）日：2014-12-25

  The invention feature series of benzothiazole derivatives as potent immunosuppressive and antiinflammatory agents. Eight compounds 2, 4, 5, 8, 9, 10, 12, and 18 showed potent inhibitory activity on PHA-activated T-cell proliferation. Compounds 2, 4, 8, and 18 were found to have a potent inhibitory activity with IC 50 values ranging <1.0-2.9 μg/mL against IL-2. Studies on innate immune response revealed that compounds 2, 8, 9, and 10 have significant suppressive effect on ROS production with an IC 50 values 1.9, <1, 3.7 and 1.1 μg/mL, respectively. The LPS-induced nitrites in J774 macrophages cell line was inhibited by 4, 8, 9, and 18 at a concentration of 25 μg/mL (56-91%). In addition compounds 5, 8, 12, and 18 showed potent suppression on interleukin 4 (IL-4), particularly 9 (IC 50 <1 μg/mL). No cytotoxicity was found except for compound 9 and 18 (11.4 and 10.4 μg/mL IC 50 ), respectively.

  苯并噻唑衍生物系列的发明特征作为强效免疫抑制剂和抗炎剂。八种化合物2、4、5、8、9、10、12和18表现出对PHA激活的T细胞增殖具有强效的抑制活性。发现化合物2、4、8和18在IL-2上有强效的抑制活性，IC50值范围在<1.0-2.9 μg/mL之间。对先天免疫反应的研究显示，化合物2、8、9和10对ROS产生具有显著的抑制作用，其IC50值分别为1.9、<1、3.7和1.1 μg/mL。J774巨噬细胞系中LPS诱导的亚硝酸盐在25 μg/mL浓度下被化合物4、8、9和18抑制（56-91%）。此外，化合物5、8、12和18对白细胞介素4（IL-4）表现出强效的抑制作用，尤其是9（IC50<1 μg/mL）。除了化合物9和18（分别为11.4和10.4 μg/mL的IC50），未发现细胞毒性。
• A highly selective fluorescent probe for fast detection of hydrogen sulfide in aqueous solution and living cells
  作者：Zheng Xu、Lin Xu、Ji Zhou、Yufang Xu、Weiping Zhu、Xuhong Qian

  DOI：10.1039/c2cc36141h

  日期：——

  fluorescence probe E1 based on an excited-state intramolecular proton transfer (ESIPT) mechanism for detection of hydrogen sulfide (H(2)S) is reported. E1 responds to H(2)S quickly and showed a 30-fold fluorescence enhancement in 2 minutes. Moreover, E1 can detect H(2)S quantitatively with a detection limit as low as 0.12 muM in aqueous solution. Its potential for biological applications was confirmed

  报道了一种基于激发态分子内质子转移（ESIPT）机理的新型比例荧光探针E1，用于检测硫化氢（H（2）S）。E1快速响应H（2）S，并在2分钟内显示30倍荧光增强。此外，E1可以定量检测H（2）S，其检测限低至水溶液中的0.12μM。通过将其用于活细胞中H（2）S的荧光成像，证实了其在生物应用中的潜力。
• A simple and eco-friendly process catalyzed by montmorillonite K-10, with air as oxidant, for synthesis of 2-substituted benzothiazoles
  作者：Guo Feng Chen、Nan Xiao、Jing Sen Yang、Hong Yang Li、Bao Hua Chen、Li Fen Han

  DOI：10.1007/s11164-014-1619-4

  日期：2015.8

  Simple and eco-friendly synthesis of 2-substituted benzothiazoles is described. The reaction is performed in absolute ethanol at room temperature, using a catalytic amount of montmorillonite K-10, and with continuous bubbling of air as oxidant. Simplicity, ease of handling of the system, an environmentally friendly and reusable catalyst, a plentiful, inexpensive, and safe oxidant, and mild conditions are the main advantages of this procedure.

  描述了一种简单且环保的合成2-取代苯并噻唑的方法。反应在室温下的无水乙醇中进行，使用催化量的蒙脱土K-10，并持续通入空气作为氧化剂。该方法的主要优点是操作简单、系统易于处理、催化剂环保且可重复使用、氧化剂丰富、廉价且安全，以及反应条件温和。
• 一种检测高碘酸根的高选择性比值型荧光探 针
  申请人：上海师范大学

  公开号：CN105315228B

  公开（公告）日：2019-09-06

  本发明提供一种检测高碘酸根的高选择性比值型荧光探针，具有下式I所示结构，其中R1选自H或C1‑C4烷基；R2选自相邻的两个碳分别被1个羟基取代的C2‑C8烷基；R3选自H和C1‑C4烷基；和R4选自H和C1‑C4烷基。本发明还包括用于制备该式I化合物的中间体式II化合物、制备式I化合物的方法、含有式I化合物的检测组合物和检测试剂盒以及式I化合物作为荧光探针在检测化学体系中的高碘酸根、生物活细胞内高碘酸根的荧光成像测试、高通量水解酶测试平台的构建以及检测试纸条的开发中的应用。