2-(2′-hydroxy-3′-ethoxyphenyl)benzothiazole | 1323863-85-9

• 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′-hydroxy-3′-ethoxyphenyl)benzothiazole
• 英文别名: (2-(benzo[d]thiazol-2-yl)-6-ethoxyphenol)；2-(1,3-benzothiazol-2-yl)-6-ethoxyphenol；2-(1,3-Benzothiazol-2-yl)-6-ethoxyphenol
• CAS: 1323863-85-9
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: YFJHVNDZXAIOTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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′-ethoxyphenyl)benzothiazole 、 2,4-二硝基氟苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以83%的产率得到
  参考文献：
  名称：

  基于ESIPT的荧光探针，用于高选择性检测水溶液和活细胞中的谷胱甘肽

  摘要：

  本文中的高灵敏度和选择性荧光探针1基于对2-（2'-羟基-3'-乙氧基苯基）苯并噻唑的激发态分子内质子转移（ESIPT）过程的调节，设计并合成了GSH。将GSH引入含有CTAB胶束的中性溶液中后，探针的保护基二硝基苯基通过亲核取代被去除，从而回收了2-（2'-羟基-3'-乙氧基苯基）苯并噻唑的ESIPT过程，从而导致485 nm处的荧光增强。此外，探针的荧光强度与GSH浓度在0到100μM之间成线性比例，并且获得的检测限低至0.81μM。相对于Cys和Hcy，对GSH的选择性提高还归因于GSH中的一个以上的羧基。重要的是，该探针已成功用于监测活HeLa细胞中的GSH。

  DOI：

  10.1016/j.dyepig.2016.02.027
• 作为产物：
  描述：

  3-乙氧基-2-羟基苯甲酸 、 2-氨基苯硫醇 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到2-(2′-hydroxy-3′-ethoxyphenyl)benzothiazole
  参考文献：
  名称：

  基于ESIPT的荧光探针，用于高选择性检测水溶液和活细胞中的谷胱甘肽

  摘要：

  本文中的高灵敏度和选择性荧光探针1基于对2-（2'-羟基-3'-乙氧基苯基）苯并噻唑的激发态分子内质子转移（ESIPT）过程的调节，设计并合成了GSH。将GSH引入含有CTAB胶束的中性溶液中后，探针的保护基二硝基苯基通过亲核取代被去除，从而回收了2-（2'-羟基-3'-乙氧基苯基）苯并噻唑的ESIPT过程，从而导致485 nm处的荧光增强。此外，探针的荧光强度与GSH浓度在0到100μM之间成线性比例，并且获得的检测限低至0.81μM。相对于Cys和Hcy，对GSH的选择性提高还归因于GSH中的一个以上的羧基。重要的是，该探针已成功用于监测活HeLa细胞中的GSH。

  DOI：

  10.1016/j.dyepig.2016.02.027

文献信息

• 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。
• Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking
  作者：Khalid Mohammed Khan、Fazal Rahim、Sobia Ahsan Halim、Muhammad Taha、Momin Khan、Shahnaz Perveen、Zaheer-ul-Haq、Muhammad Ahmed Mesaik、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2011.05.052

  日期：2011.7

  active analogs were also evaluated for cytotoxicity and none of the compounds showed any cytotoxic effect. Furthermore, molecular docking studies were performed using the gold 3.0 program to investigate the binding mode of benzothiazole derivatives. This study identifies a novel class of β-glucuronidase inhibitors.

  苯并噻唑衍生物1 - 26已被合成和它们在体外β葡萄糖醛酸酶的潜力进行了评估。化合物4（IC 50  = 8.9±0.25μM），5（IC 50  = 36.1±1.80μM），8（IC 50  = 8.9  ±  0.38μM），13（IC 50  = 19.4±1.00μM），16（IC 50  = 4.23±0.054μM）和18（IC 50  = 2.26±0.06μM）显示β-葡糖醛酸糖苷酶活性强于标准品（d-蔗糖1,4-内酯，IC 50 = 48.4±1.25μM）。化合物9（IC 50  = 94.0±4.16μM）被发现是该系列中活性最低的化合物。还评估了所有活性类似物的细胞毒性，没有一种化合物显示出任何细胞毒性作用。此外，使用Gold 3.0程序进行了分子对接研究，以研究苯并噻唑衍生物的结合模式。这项研究确定了一类新型的β-葡萄糖醛酸苷酶抑制剂。
• One-Pot Synthesis of Benzothiazole-Tethered Chromanones/Coumarins via Claisen Rearrangement Using the Solid State Melt Reaction
  作者：Manickam Bakthadoss、Raman Selvakumar

  DOI：10.1021/acs.joc.5b02920

  日期：2016.4.15

  A novel protocol has been successfully established for the efficient synthesis of benzothiazole-tethered chromanone/coumarin scaffolds via Claisen rearrangement using a solid state melt reaction in a one-pot manner. Benzothiazole formation and Claisen rearrangement involve the cleavage of S–S and C–O bonds and formation of C–S, C═N, and C–C bonds in a single operation without using a catalyst or solvent

  已经成功地建立了一种新的方案，该方案通过使用固态熔融反应以一锅方式通过克莱森重排有效合成苯并噻唑系链的苯并二氢吡喃酮/香豆素支架。苯并噻唑的形成和克莱森重排涉及在不使用催化剂或溶剂的情况下，一次操作中S–S和C–O键的裂解以及C–S，C═N和C–C键的形成。
• The immunomodulation potential of the synthetic derivatives of benzothiazoles: Implications in immune system disorders through in vitro and in silico studies
  作者：Khalid Mohammed Khan、Mohammad A. Mesaik、Omer M. Abdalla、Fazal Rahim、Samreen Soomro、Sobia A. Halim、Ghulam Mustafa、Nida Ambreen、Ahmad Shukralla Khalid、Muhammad Taha、Shahnaz Perveen、Muhammad Tanveer Alam、Abdul Hameed、Zaheer Ul-Haq、Hayat Ullah、Zia Ur Rehman、Rafat Ali Siddiqui、Wolfgang Voelter

  DOI：10.1016/j.bioorg.2015.11.004

  日期：2016.2

  Benzothiazole and its natural or synthetic derivatives have been used as precursors for several pharmacological agents for neuroprotective, anti-bacterial, and anti-allergic activities. The objecctive of the present study was to evaluate effects of benzothiazole analogs (compounds 1-26) for their immunomodulatory activities. Eight compounds (2, 4, 5, 8-10, 12, and 18) showed potent inhibitory activity on PHA-activated peripheral blood mononuclear cells (PBMCs) with IC50 ranging from 3.7 to 11.9 mu M compared to that of the standard drug, prednisolone <1.5 mu M. Some compounds (2, 4, 8, and 18) were also found to have potent inhibitory activities on the production of IL-2 on PHA/PMA-stimulated PBMCs with IC50 values ranging between <4.0 and 12.8 mu M. The binding interaction of these compounds was performed through silico molecular docking. Compounds 2, 8, 9, and 10 significantly suppressed oxidative burst ROS production in phagocytes with IC50 values between <4.0 and 15.2 mu M. The lipopolysaccharide (LPS)-induced nitrites in murine macrophages cell line J774 were found to be inhibited by compounds 4, 8, 9, and 18 at a concentration of 25 mu g/mL by 56%, 91%, 58%, and 78%, respectively. Furthermore, compounds 5, 8, 12, and 18 showed significant (P < 0.05) suppressive activity on Th-2 cytokine, interleukin 4 (IL-4) with an IC50 range of <4.0 to 40.3 mu M. Interestingly compound 4 has shown a selective inhibitory activity on IL-2 and T cell proliferation (naive T cell proliferation stage) rather than on IL-4 cytokine, while compound 12 displayed an interference with T-cell proliferation and IL-4 generation. Moreover compound 8 and 18 exert non-selective inhibition on both IL-2 and IL-4 cytokines, indicating a better interference with stage leading to humoral immune response and hence possible application in autoimmune diseases. (C) 2015 Elsevier Inc. All rights reserved.
• Theoretical studies, Hirshfeld surface analysis, and crystal structure determination of a newly synthesized benzothiazole copper(II) complex
  作者：Hadi Kargar、Muhammad Ashfaq、Mehdi Fallah-Mehrjardi、Reza Behjatmanesh-Ardakani、Khurram Shahzad Munawar、Muhammad Nawaz Tahir

  DOI：10.1016/j.molstruc.2022.132905

  日期：2022.8