N-(3-溴苯基)-4-甲氧基苯甲酰胺 | 301158-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-溴苯基)-4-甲氧基苯甲酰胺
• 英文名称: N-(3-Bromo-phenyl)-4-methoxy-benzamide
• 英文别名: N-(3-bromophenyl)-4-methoxybenzamide
• CAS: 301158-03-2
• 化学式: C₁₄H₁₂BrNO₂
• mdl: MFCD01011475
• 分子量: 306.159
• InChiKey: UYKRKRIEVVRACV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-溴苯基)-4-甲氧基苯甲酰胺 在 劳森试剂 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以45.1%的产率得到N-(3-bromophenyl)-4-methoxybenzenecarbothioamide
  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
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 间溴苯胺 在 吡啶 作用下， 反应 2.0h， 以42.2%的产率得到N-(3-溴苯基)-4-甲氧基苯甲酰胺
  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

• Likhomanenko, E. E.; Shpan'ko, I. V.; Litvinenko, L. M., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 12, p. 2341 - 2347
  作者：Likhomanenko, E. E.、Shpan'ko, I. V.、Litvinenko, L. M.、Goncharov, A. N.

  DOI：——

  日期：——
• 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.