5-chloro-2-(4-ethoxyphenyl)benzothiazole

• 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-chloro-2-(4-ethoxyphenyl)benzothiazole
• 英文别名: 5-Chloro-2-(4-ethoxyphenyl)benzo[d]thiazole；5-Chloro-2-(4-ethoxyphenyl)-1,3-benzothiazole；5-chloro-2-(4-ethoxyphenyl)-1,3-benzothiazole
• 化学式: C₁₅H₁₂ClNOS
• 分子量: 289.785
• InChiKey: AJKDFBCTGMJQSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙氧基苯甲醛 、 2-氨基-4-氯苯硫醇 在 硝酸脲 作用下， 以 neat (no solvent, solid phase) 为溶剂， 以92%的产率得到5-chloro-2-(4-ethoxyphenyl)benzothiazole
  参考文献：
  名称：

  硝酸尿素催化的C-N和C-S键形成：5-氯-2-芳基苯并[d]噻唑衍生物的机械化学方法

  摘要：

  使用4-氯-2-氨基苯硫酚和芳香醛在硝酸尿素作为催化剂的情况下，使用机械化学砂轮技术合成了一系列取代的5-氯-2-芳基苯并[d]噻唑。该方案有效地在室温下在无金属条件下进行，并且可以在较短的反应时间（30-60 s）内以高收率或优异的收率获得所需的产物。所有合成的衍生物的结构通过光谱表征证实。设计的方案具有多个优点，例如环保，无溶剂，高收率，易于后处理和催化剂的可回收性。催化剂可重复使用至少四次，而活性没有明显损失。已经证明了一系列衍生物具有良好的官能团耐受性。

  DOI：

  10.1002/jhet.4224

文献信息

• Synthesis, and In Vitro and In Silico α-Glucosidase Inhibitory Studies of 5-Chloro-2-Aryl Benzo[d]thiazoles
  作者：Shazia Shah、Arshia、Kulsoom Javaid、Humaira Zafar、Khalid Mohammed Khan、Ruqaiya Khalil、Zaheer Ul-Haq、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bioorg.2018.02.013

  日期：2018.8

  Twenty-five derivatives of 5-chloro-2-aryl benzo[d]thiazole (1-25) were synthesized and evaluated for their alpha-glucosidase (S. cerevisiae EC 3.2.1.20) inhibitory activity in vitro. Among them eight compounds showed potent activity with IC50 values between 22.1 +/- 0.9 and 136.2 +/- 5.7 mu M, when compared with standard acarbose (IC50 = 840 +/- 1.73 mu M). The most potent compounds 4, 9, and 10 showed IC50 values in the range of 22.1 +/- 0.9 to 25.6 +/- 1.5 mu M. Compounds 2, 5, 11, and 19 showed IC50 values within the range of 40.2 +/- 0.5 to 60.9 +/- 2.0 mu M. Compounds 1 and 3 were also found to be good inhibitors with IC50 values 136.2 +/- 5.7 and 104.8 +/- 9.9 lM, respectively. Their activities were compared with alpha-glucosidase inhibitor drug acarbose (standard) (IC50 = 840 +/- 1.73 mu M). The remaining compounds were inactive. Structure-activity relationships (SAR) have also been established. Kinetics studies indicated compounds 2, 3, 10, 19, and 25 to be non-competitive, while 1, 5, 9, and 11 as competitive inhibitors of alpha-glucosidase enzyme. All the active compounds (1-5, 9-11, and 19) were also found to be non-cytotoxic, in comparison to the standard drug i.e., doxorubicin (IC50 = 0.80 +/- 0.12 mu M) in MTT assay. Furthermore, molecular interactions of active compounds with the enzyme binding sites were predicted through molecular modeling studies. (C) 2018 Elsevier Inc. All rights reserved.
• Urea nitrate–catalyzed <scp>C‐N</scp> and <scp>C‐S</scp> bond formation: A mechanochemical approach for <scp>5‐chloro</scp> ‐2‐arylbenzo <i>[d]</i> thiazole derivatives
  作者：Ayushi Sethiya、Nusrat Sahiba、Jay Soni、Shikha Agarwal

  DOI：10.1002/jhet.4224

  日期：2021.3

  A series of substituted 5‐chloro‐2‐arylbenzo[d]thiazoles were synthesized using 4‐chloro‐2‐aminothiophenol and aromatic aldehydes in the presence of urea nitrate as a catalyst using the mechanochemical grindstone technique. This protocol was effectively carried out under metal‐free conditions at room temperature, and the desired products were obtained in high to excellent yields in short reaction time

  使用4-氯-2-氨基苯硫酚和芳香醛在硝酸尿素作为催化剂的情况下，使用机械化学砂轮技术合成了一系列取代的5-氯-2-芳基苯并[d]噻唑。该方案有效地在室温下在无金属条件下进行，并且可以在较短的反应时间（30-60 s）内以高收率或优异的收率获得所需的产物。所有合成的衍生物的结构通过光谱表征证实。设计的方案具有多个优点，例如环保，无溶剂，高收率，易于后处理和催化剂的可回收性。催化剂可重复使用至少四次，而活性没有明显损失。已经证明了一系列衍生物具有良好的官能团耐受性。