6-fluoro-2-(4-methoxyphenyl)benzo[d]thiazole

• 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: 6-fluoro-2-(4-methoxyphenyl)benzo[d]thiazole
• 英文别名: 6-fluoro-2-(4-methoxyphenyl)benzothiazole；6-Fluoro-2-(4-methoxyphenyl)-1,3-benzothiazole
• 化学式: C₁₄H₁₀FNOS
• 分子量: 259.304
• InChiKey: JGSGKOGXLCLHML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-氟苯基)-4-甲氧基苯甲酰胺 在 劳森试剂 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 氯苯 为溶剂， 反应 3.0h， 生成 6-fluoro-2-(4-methoxyphenyl)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors

  摘要：

  Protein tyrosine kinases occupy a central position in the control of cellular proliferation and its inactivation might lead to the discovery of a new generation anticancer compounds. Substituted benzothiazoles have been found to mimic the ATP-competitive binding of genistein and quercetin to tyrosine kinase. A series of novel 2-phenyl-1,3-benzothiazoles were synthesized and characterised by IR, H-1 NMR and mass spectroscopy. All the compounds were tested for their anticancer activity against MCF-7 breast cancer cell line with the MTT assay. Most of the compounds showed moderate to good anti-breast cancer activity. Anticancer activity varied with substitution on the benzothiazole nucleus with halogens and at 4 position, substitution of the 2-phenyl moiety with methyl and methoxy groups was also explored. Among the compounds tested with MTT assay, mono fluoro substitution on benzothiazole nucleus and 4'-methyl variations at 2-phenyl position demonstrated highest percent growth inhibition of MCF-7 cells. Docking studies of the synthesised compounds was done on EGFR using GRIP batch docking method to study their observed activity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmgm.2010.04.003

文献信息

• Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
  作者：Amrita Dey、Alakananda Hajra

  DOI：10.1021/acs.orglett.9b00245

  日期：2019.3.15

  A highly efficient method for the synthesis of 2-arylbenzothiazoles has been developed using readily available aromatic amines, benzaldehydes, and NH4SCN as a sulfur source. A library of 2-arylbenzothiazoles with wide functional group compatibility has been synthesized in good yields through iodine-mediated oxidative annulation.

  已经开发了一种高效的合成2-芳基苯并噻唑的方法，该方法使用容易获得的芳族胺，苯甲醛和NH 4 SCN作为硫源。通过碘介导的氧化环化反应，以高收率合成了具有广泛官能团相容性的2-芳基苯并噻唑文库。
• An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring
  作者：Ashley A. Weekes、Mark C. Bagley、Andrew D. Westwell

  DOI：10.1016/j.tet.2011.08.004

  日期：2011.10

  focus on their unsubstituted ring counterparts. Here we describe a new concise and efficient synthetic route to biologically relevant 2-phenylbenzothiazoles in high yield from the reaction of substituted 2-aminothiophenol disulfides and benzaldehydes, promoted by the inexpensive and non-toxic inorganic oxidant sodium metabisulfite in DMSO at 120 °C. Our new method is tolerant of a range of substituents

  某些在苯并噻唑环上含有取代基的2-苯基苯并噻唑具有重要的生物学特性，但是迄今为止描述的2-苯基苯并噻唑的大多数合成方法都集中在它们的未取代环对应物上。在这里，我们描述了一种新的简洁有效的合成路线，该路线是由廉价的且无毒的无机氧化剂偏亚硫酸氢钠在DMSO中于120°C促进的，是由取代的2-氨基硫代苯酚二硫化物与苯甲醛的反应以高收率获得生物相关的2-苯基苯并噻唑的新方法。我们的新方法可耐受苯并噻唑和苯环上的一系列取代基，并且无需柱色谱即可有效获得取代的2-苯基苯并噻唑。
• Synthesis of Benzothiazoles through Copper-Catalyzed One-Pot Three-Component Reactions with Use of Sodium Hydrosulfide as a Sulfur Surrogate
  作者：Namjin Park、Yumi Heo、Manian Rajesh Kumar、Yong Kim、Kwang Ho Song、Sunwoo Lee

  DOI：10.1002/ejoc.201101773

  日期：2012.4

  Copper-catalyzed one-pot three-component reactions of 2-iodoanilines, aldehydes, and NaSH·n H2O afford benzothiazoles in good yields. When CuCl was employed as a catalyst in the absence of a ligand, a variety of aromatic aldehydes and substituted 2-iodoanilines reacted with NaSH·n H2O to produce the corresponding 2-arylbenzothiazoles in 70–98 % yields. The copper catalyst plays a key role in C–S bond

  铜催化的 2-碘苯胺、醛和 NaSH·n H2O 的一锅三组分反应以良好的收率提供苯并噻唑。当在没有配体的情况下使用 CuCl 作为催化剂时，各种芳香醛和取代的 2-碘苯胺与 NaSH·n H2O 反应生成相应的 2-芳基苯并噻唑，产率为 70-98%。铜催化剂在 NaSH·n H2O 和由 2-碘苯胺和醛缩合形成的芳基碘之间形成 C-S 键中起关键作用。研究发现，NaSH·n H2O 在苯并噻唑的形成过程中起硫替代物和氧化剂的作用。
• Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles
  作者：D. Bose、Mohd. Idrees

  DOI：10.1055/s-0029-1218798

  日期：2010.6

  approach represents a practical and atom-economical approach for regio­selective and metal-free cascade synthesis of substituted benzothiazoles. This one-pot, environmentally benign protocol involves 2-fluoroanilines, benzoyl chlorides and Lawesson’s reagent under microwave irradiation (5 min) or conventional thermal conditions (3 h). benzothiazole - metal-free - cascade reactions - S-arylation - regioselective

  碳-氟键裂变与无金属条件下的CS键形成有关，这在文献中很少报道。分子内CS键形成反应发生原位的碳-氟键的裂变，并且被认为通过S进行Ñ氩机制。该方法代表了对取代的苯并噻唑的区域选择性和无金属级联合成的实用且原子经济的方法。这种一锅法的环境友好协议涉及2-氟苯胺，苯甲酰氯和Lawesson试剂在微波辐射（5分钟）或常规热条件（3小时）下的处理。 苯并噻唑-无金属-级联反应-S-芳基化-区域选择性
• Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization
  作者：Bokka Srinivas、Kotari Shakeena、Durgeswari Lakkavarapu Kota、Valeti Abhinav、Pyla Eswar、Rongali Geetha Sravani、Anandam Sampath Pavan Kumar、Kiran Indukuri、Kumpatla Ayyappa Dhanaraju、Muthyala Murali Krishna Kumar、Santhosh Kumar Alla

  DOI：10.1021/acs.joc.2c03078

  日期：——

  for the preparation of 2-arylbenzothiazoles using aryl isothiocyanates and electron-rich arenes. The synthetic route involves triflic acid promoted addition of the arenes to aryl isothiocyanates followed by FeCl3-catalyzed C–S bond formation via C–H functionalization. The approach provides the advantage of synthesis of benzothiazoles without the conventional use of aryl aldehyde/carboxylic acid precursors

  我们在此报告了使用芳基异硫氰酸酯和富电子芳烃制备 2-芳基苯并噻唑的直接合成路线。合成路线包括三氟甲磺酸促进芳烃加成异硫氰酸芳基酯，然后通过C-H 官能化形成FeCl 3催化的 C-S 键。该方法提供了合成苯并噻唑的优势，而无需使用较便宜的铁 (III) 催化剂常规使用芳基醛/羧酸前体。