5-(1,3-benzothiazol-2-yl)-1,2,4-benzenetriol | 1323864-02-3

• 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: 5-(1,3-benzothiazol-2-yl)-1,2,4-benzenetriol
• 英文别名: 2-(2,4,5-trihydroxyphenyl)-benzo[d]thiazole；5-(1,3-Benzothiazol-2-yl)benzene-1,2,4-triol；5-(1,3-benzothiazol-2-yl)benzene-1,2,4-triol
• CAS: 1323864-02-3
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: MFMCXBGEUIDIID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 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：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,5-三羟基苯甲醛 、 2-氨基苯硫醇 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以51%的产率得到5-(1,3-benzothiazol-2-yl)-1,2,4-benzenetriol
  参考文献：
  名称：

  设计，合成和评估作为多功能试剂的苯并噻唑衍生物。

  摘要：

  氧化应激是多种多因素疾病的产物或病因。另一方面，开发多功能化合物是控制复杂疾病的公认策略。为此，合成了一系列苯并噻唑衍生物并评估了其作为抗氧化剂，防晒霜（过滤剂），抗真菌剂和抗增殖剂的多功能功效。通过2-氨基硫酚与不同的苯甲醛之间的缩合反应可轻松合成化合物。SAR研究，特别是在苯并噻唑的2位和6位上，对4g和4k的鉴定为多功能药物设计中非常有趣的潜在化合物。特别是化合物4g是在HEK 293细胞中表达的hERG钾通道的最佳阻滞剂，具有60.32％的抑制作用，IC 50  = 4.79μM。

  DOI：

  10.1016/j.bioorg.2020.103960

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。
• 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.
• Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
  作者：Ernestine Nicaise Djuidje、Sabrina Sciabica、Raissa Buzzi、Valeria Dissette、Jan Balzarini、Sandra Liekens、Elena Serra、Elisa Andreotti、Stefano Manfredini、Silvia Vertuani、Anna Baldisserotto

  DOI：10.1016/j.bioorg.2020.103960

  日期：2020.8

  aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized

  氧化应激是多种多因素疾病的产物或病因。另一方面，开发多功能化合物是控制复杂疾病的公认策略。为此，合成了一系列苯并噻唑衍生物并评估了其作为抗氧化剂，防晒霜（过滤剂），抗真菌剂和抗增殖剂的多功能功效。通过2-氨基硫酚与不同的苯甲醛之间的缩合反应可轻松合成化合物。SAR研究，特别是在苯并噻唑的2位和6位上，对4g和4k的鉴定为多功能药物设计中非常有趣的潜在化合物。特别是化合物4g是在HEK 293细胞中表达的hERG钾通道的最佳阻滞剂，具有60.32％的抑制作用，IC 50  = 4.79μM。