2'-fluoro-4-methylbenzothioanilide | 146274-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-fluoro-4-methylbenzothioanilide
• 英文别名: N-(2-fluorophenyl)-4-methylbenzenecarbothioamide
• CAS: 146274-08-0
• 化学式: C₁₄H₁₂FNS
• 分子量: 245.32
• InChiKey: HAVPXUOHJINUBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2'-fluoro-4-methylbenzothioanilide 在 氢氧化钾 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 6.0h， 以41%的产率得到4-fluoro-2-(4-methylphenyl)benzothiazole
  参考文献：
  名称：

  Novel Disease-Modifying Antirheumatic Drugs. I. Synthesis and Antiarthritic Activity of 2-(-4-Methylphenyl)benzothiazoles.

  摘要：

  合成了一系列 2-(4-甲基苯基)苯并噻唑，并使用佐剂诱导的关节炎大鼠模型进行了评估。在佐剂诱导的关节炎大鼠模型中，4-乙酰氧基-2-（4-甲基苯基）苯并噻唑（7m），即 KB-2683 的药效最强，因此被选为进一步评估的对象。与非类固醇抗炎药物相比，化合物 7m 没有显示出抗炎或镇痛活性。不过，它在增强型迟发型超敏反应中显示出了免疫调节活性。

  DOI：

  10.1248/cpb.40.2387
• 作为产物：
  描述：

  N-(2-氟苯基)-4-甲基苯甲酰胺 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以53%的产率得到2'-fluoro-4-methylbenzothioanilide
  参考文献：
  名称：

  Novel Disease-Modifying Antirheumatic Drugs. I. Synthesis and Antiarthritic Activity of 2-(-4-Methylphenyl)benzothiazoles.

  摘要：

  合成了一系列 2-(4-甲基苯基)苯并噻唑，并使用佐剂诱导的关节炎大鼠模型进行了评估。在佐剂诱导的关节炎大鼠模型中，4-乙酰氧基-2-（4-甲基苯基）苯并噻唑（7m），即 KB-2683 的药效最强，因此被选为进一步评估的对象。与非类固醇抗炎药物相比，化合物 7m 没有显示出抗炎或镇痛活性。不过，它在增强型迟发型超敏反应中显示出了免疫调节活性。

  DOI：

  10.1248/cpb.40.2387

文献信息

• Novel Disease-Modifying Antirheumatic Drugs. I. Synthesis and Antiarthritic Activity of 2-(-4-Methylphenyl)benzothiazoles.
  作者：Noriyuki HORI、Goro TSUKAMOTO、Atsushi IMAMURA、Masami OHASHI、Tadayuki SAITO、Kohichiro YOSHINO

  DOI：10.1248/cpb.40.2387

  日期：——

  A series of 2-(4-methylphenyl)benzothiazoles was synthesized and evaluated using an adjuvant-induced arthritic rat model. This calss of desired compounds affecting the immune response was found using hemagglutination assay.4-Acetoxy-2-(4-methylphenyl)benzothiazole (7m), KB-2683, was most potent in the adjuvant-induced arthritic rat model and selected for further evalution. In contrast to nonsteroidal antiinflammatory drugs, compound 7m showed no antiinflammatory or analgesic activities. It did, however, show an immunomodulatory activity in enhanced delayed type hypersensitivity.

  合成了一系列 2-(4-甲基苯基)苯并噻唑，并使用佐剂诱导的关节炎大鼠模型进行了评估。在佐剂诱导的关节炎大鼠模型中，4-乙酰氧基-2-（4-甲基苯基）苯并噻唑（7m），即 KB-2683 的药效最强，因此被选为进一步评估的对象。与非类固醇抗炎药物相比，化合物 7m 没有显示出抗炎或镇痛活性。不过，它在增强型迟发型超敏反应中显示出了免疫调节活性。
• Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors
  作者：Hemal A. Bhuva、Suvarna G. Kini

  DOI：10.1016/j.jmgm.2010.04.003

  日期：2010.8

  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.