5-chloro-2-(furan-2-yl)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-(furan-2-yl)benzothiazole
• 英文别名: 5-Chloro-2-(furan-2-yl)benzo[d]thiazole；5-Chloro-2-(furan-2-yl)-1,3-benzothiazole
• 化学式: C₁₁H₆ClNOS
• 分子量: 235.694
• InChiKey: BVJPEIHFIKNFCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 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：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(furan-2-yl)benzothiazole 、 二苯基乙炔 在 silver tetrafluoroborate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以86%的产率得到
  参考文献：
  名称：

  阳离子钌（II）配合物配体辅助的杂芳基C（sp2）-H键活化，用于由生物相关杂环指导的炔烃与炔烃的烯基化

  摘要：

  杂芳烃与炔烃的烯基化反应是通过配体辅助的杂芳基C（sp 2）-H键活化而实现的，该活化是由生物相关的杂环骨架苯并噻唑和苯并恶唑控制的原位生成的阳离子Ru II复合物实现的，因此杂芳烃的应用范围很广噻吩，呋喃，N-甲基吡咯和3-吲哚）和炔烃（二芳基，二烷基和芳基烷基）的收率高，立体和区域选择性高。

  DOI：

  10.1002/cctc.201701016
• 作为产物：
  描述：

  2,2'-联糠醛 、 2-氨基-4-氯苯硫醇 在 silica gel-supported chlorosulfonic acid 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 4.5h， 以85.5%的产率得到5-chloro-2-(furan-2-yl)benzothiazole
  参考文献：
  名称：

  一种苯并噻唑衍生物的合成方法

  摘要：

  本发明涉及一种苯并噻唑衍生物的合成方法，所述方法包括在有机溶剂中，于催化剂和任选的促进剂的存在下，使羟基酮化合物与2‑氨基苯硫酚发生反应而合成得到所述苯并噻唑衍生物。所述方法具有产率高、纯度高、后处理简单等诸多优点，为苯并噻唑衍生物的合成提供了新的路线和方法，具有良好的应用潜力和研究价值。

  公开号：

  CN104557768B

文献信息

• Bis(μ-thiolato)-dicopper Containing Fully Spin Delocalized Mixed Valence Copper–Sulfur Clusters and Their Electronic Structural Properties with Relevance to the Cu_A Site
  作者：Saikat Mishra、Anirban Bhandari、Devender Singh、Rajeev Gupta、Marilyn M. Olmstead、Apurba K. Patra

  DOI：10.1021/acs.inorgchem.1c00075

  日期：2021.4.19

  architecture to 1. The spectroscopic properties and the X-ray structures revealed that 2–4 are fully spin delocalized mixed valence (MV) of class-III type clusters. The structural parameters of the N2Cu2μ-S(R)}2 units of 3 and 4 closely resemble those of the MV binuclear CuA site. With the aid of UV–vis-NIR, EPR, and spectroelectrochemical studies, the electronic properties of these complexes have been described

  具有芳族和脂肪族硫醇-S供体席夫碱配体，铜-硫簇，[（L1）8 Cu I 6 Cu II 2 ]（ClO 4）2 ·DMF·0.5CH 3 OH（1）和[（L2）12铜我5的Cu II 11（μ 4 -S）（μ 4 -O）6 ]（CLO 4）·4H 2 O，已经分别报道（化学COMMUN。 2017，53，3334）; HL1 / HL2是2-（（（（3-甲基噻吩-2-基）亚甲基）氨基）苯）/乙硫醇）。复杂的图1包括由互连的Cu 2 μ-S（R）} 2单元组成的轮状Cu 8 S 8框架。要了解与Cu A位点相关的性质，并检查自组装是否生成与1个，三个配合物[（L3）8 Cu I 6 Cu II 2 ]（ClO 4）2 ·（C 2 H 5）2 O·2.5H 2 O（2），[（L3 Cl）8 Cu I 6 CuII 2 ]（ClO 4）2 ·1.25（C 2 H 5）2 O·1.25CH 3
• p -Toluenesulfonic acid-catalyzed metal-free formal [4 + 1] heteroannulation via N H/O H/S H functionalization: One-pot access to 2-aryl/hetaryl/alkyl benzazole derivatives
  作者：Abhijeet Srivastava、Gaurav Shukla、Maya Shankar Singh

  DOI：10.1016/j.tet.2016.12.073

  日期：2017.2

  concise and direct one-pot [4 + 1] synthetic strategy for the construction of 2-substituted benzazoles such as benzoxazoles and benzothiazoles has been disclosed in high yields (80–98%) by cascade coupling reaction of 2-amino(thio)phenols with β-oxodithioesters. The current approach enables NH/OH/SH functionalization in one-pot under solventless condition leading to diverse benzazoles without use of any

  通过2-氨基（硫代）的级联偶联反应，已公开了一种高产率（80-98％）的简洁，直接的一锅[4 +1]合成策略，用于构建2-取代的苯并唑，如苯并恶唑和苯并噻唑酚与β-氧二硫代酯。目前的方法可以在无溶剂条件下在一锅中实现N H / O H / S H官能化，从而无需使用任何外部金属即可产生多种苯并恶唑。各种各样的2-氨基（硫代）酚和β-氧二硫代酯均具有出色的官能团耐受性，可用于该转化。此外，我们通过证明其与DNA拓扑异构酶II抑制剂的多样化多样化的相容性，抢占了这一新策略的广泛含义。
• 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。
• Na2S2O4-Mediated Cyclocondensations of 2,2′-Disulfanediyldi- anilines with Aldehydes: A Facile and Inexpensive Method for the Synthesis of 2-Substituted Benzothiazoles
  作者：Zhanglin Wang、Riyuan Tang、Qin Xiao

  DOI：10.1002/cjoc.201190084

  日期：2011.2

  A facile and inexpensive method for the synthesis of 2‐substituted benzothiazoles has been developed by Na2S2O4‐mediated cyclocondensations of 2,2′‐disulfanediyldianilines with aldehydes. In the presence of Na2S2O4 and 4 Å molecular sieves, a variety of 2‐substituted benzothiazoles were obtained from the reaction of 2,2′‐disulfanediyldianilines with aldehydes in moderate to high yields.

  Na 2 S 2 O 4介导的2,2'-二硫代二烷基二苯胺与醛的缩合反应已开发出一种简便且廉价的合成2-取代的苯并噻唑的方法。在Na 2 S 2 O 4和4Å分子筛的存在下，从2,2'-二硫代二乙二基二苯胺与醛的反应可中等至高收率获得各种2-取代的苯并噻唑。
• 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.