2-(2',3'-dihydroxyphenyl)benzothiazole | 90481-43-9

• 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: 2-(2',3'-dihydroxyphenyl)benzothiazole
• 英文别名: 6-(1,3-Benzothiazol-2(3H)-ylidene)-2-hydroxycyclohexa-2,4-dien-1-one；3-(1,3-benzothiazol-2-yl)benzene-1,2-diol
• CAS: 90481-43-9
• 化学式: C₁₃H₉NO₂S
• 分子量: 243.286
• InChiKey: CVGZLLNIXZEHRM-UHFFFAOYSA-N

物化性质

• 沸点：
  460.0±55.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(溴甲基)苯硼酸 、 2-(2',3'-dihydroxyphenyl)benzothiazole 以 aq. phosphate buffer 为溶剂， 生成
  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-苯基苯并噻唑 在 葡萄糖 、 异丙基-beta-D-硫代半乳糖吡喃糖苷 Escherichia coli JM₁₀₉ harboring plasmid pBS₂₀₇₂B 、 M₉ medium 、 维生素B1 作用下， 以74%的产率得到2-(2',3'-dihydroxyphenyl)benzothiazole
  参考文献：
  名称：

  Synthesis of vicinal diols from various arenes with a heterocyclic, amino or carboxyl group by using recombinant Escherichia coli cells expressing evolved biphenyl dioxygenase and dihydrodiol dehydrogenase genes

  摘要：

  Various aromatic molecules, in which heterocycles are linked with a phenyl or benzyl group, were converted to their respective 2,3-diols (catechols) in the benzene ring by growing cell reactions using recombinant Escherichia coli, which expressed the evolved biphenyl dioxygenase [bphA (2072)] genes and the subsequent bacterial dihydrodiol dehydrogenase (bphB) gene. These vicinal diol products showed strong in vitro inhibitory activity against the lipid peroxidation induced by free radicals and strong scavenging activity towards DPPH radicals. The vicinal diols were also synthesized from ionized monocyclic aromatics incorporating an amino or carboxyl group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.052

文献信息

• Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase
  作者：Ninad V. Puranik、Hemalata M. Puntambekar、Pratibha Srivastava

  DOI：10.1007/s00044-016-1520-3

  日期：2016.4

  Benzothiazole derivatives were synthesized and their antidiabetic potential evaluated using α-glucosidase, α-amylase, non-enzymatic glycosylation of hemoglobin and advanced glycation end product inhibition assays. Compound 3l showed low IC50 values of 0.31, 0.98, 0.59 and 0.19 mM in α-amylase, α-glucosidase, non-enzymatic glycosylation of hemoglobin and AGE inhibition assays, respectively, and outperformed

  合成了苯并噻唑衍生物，并使用α-葡萄糖苷酶，α-淀粉酶，血红蛋白的非酶糖基化和先进的糖化终产物抑制试验评估了它们的抗糖尿病潜力。化合物31在α-淀粉酶，α-葡萄糖苷酶，血红蛋白的非酶糖基化和AGE抑制试验中分别显示出0.31、0.98、0.59和0.19mM的低IC 50值，并且优于标准的阿卡波糖。酶动力学研究表明，α-淀粉酶和α-葡萄糖苷酶的K i分别为0.39和1.5 mM。3l的非键相互作用 用α-淀粉酶（3OLD）和α-葡萄糖苷酶（2ZE0）显示其结合在活性位点口袋中，并被3OLD中的残基Asp197，Glu233，Asp300和2ZE0中的Asp199，Glu256，Asp326包围。
• A ball-milling strategy for the synthesis of benzothiazole, benzimidazole and benzoxazole derivatives under solvent-free conditions
  作者：Hemant Sharma、Narinder Singh、Doo Ok Jang

  DOI：10.1039/c4gc01142b

  日期：——

  A convenient solvent-free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable ZnO-NPs via a ball-milling strategy. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low E-factor. The process is also highly efficient even on a multi-gram scale and provides easy product isolation

  通过球磨策略，使用可回收的ZnO-NP ，开发了一种方便的无溶剂合成苯并噻唑，苯并咪唑和苯并恶唑衍生物的方法。该方法提供了对环境友好的反应条件，该条件在生态规模上得分很高，而E因子却很低。该过程即使在几克规模的情况下也非常高效，并且可以轻松实现产品隔离。
• 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。
• 一种以噻唑为母体的丙烯酰酯类化合物作为荧光探针的应用及其制备方法
  申请人：西北农林科技大学

  公开号：CN109160906B

  公开（公告）日：2022-04-01

  一种以噻唑为母体的丙烯酰酯类化合物作为荧光探针的应用及其制备方法，所制备的荧光探针BTHA在二甲亚砜和4‑羟乙基哌嗪乙磺酸缓冲盐和DMSO混合溶液中，只在507nm处有荧光峰，在逐渐加入GSH后，507nm处的荧光强度不断减弱，在460nm处出现一个新的荧光峰，并且随着GSH加入峰强度随着增强，从而实现比例检测GSH，具有比率比色，高选择性检测GSH的特点；该荧光探针能够对GSH、Cys、Hcy实现特异性检测，产生不同的荧光信号，从而实现对三者进行高选择性地辨别可视化检测，且对于其他的氨基酸、阴离子和金属阳离子没有响应，具有选择性好、灵敏度高的特点，制备方法简单，易于合成。
• Anthony, Kevin; Brown, Robert G.; Hepworth, John D., Journal of the Chemical Society. Perkin transactions II, 1984, p. 2111 - 2118
  作者：Anthony, Kevin、Brown, Robert G.、Hepworth, John D.、Hodgson, Kevin W.、May, Bernadette、West, Michael A.

  DOI：——

  日期：——