N-(2-氟苯基)-4-甲氧基苯甲酰胺 | 143925-52-4

• 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-(2-氟苯基)-4-甲氧基苯甲酰胺
• 英文名称: N-(2-Fluoro-phenyl)-4-methoxy-benzamide
• 英文别名: N-(2-fluorophenyl)-4-methoxybenzamide
• CAS: 143925-52-4
• 化学式: C₁₄H₁₂FNO₂
• 分子量: 245.253
• InChiKey: NTDPONOQVIHJEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-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 4-fluoro-2-(4-methoxyphenyl)-1,3-benzothiazole
  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：

  1-叠氮基-2-氟苯 、 4-甲氧基苯甲醛 在 Co(3,5-Di^tBu-Ibu-Phyrin) 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以60%的产率得到N-(2-氟苯基)-4-甲氧基苯甲酰胺
  参考文献：
  名称：

  通过基于 Co(II) 的金属自由基催化选择性自由基胺化醛 C(sp2)-H 键与氟芳基叠氮化物：在中性和非氧化条件下由醛合成 N-氟芳基酰胺

  摘要：

  D 2h对称酰胺卟啉 3,5-Di t Bu-IbuPhyrin [Co( P1 )]的 Co( II ) 配合物已被证明是一种有效的金属基催化剂，用于 C(sp 2 )–H 键的分子间胺化醛与氟芳基叠氮化物。[Co( P1 )]-催化过程可以使用醛作为限制试剂并在中性和非氧化条件下运行，产生氮气作为唯一的副产品。金属基醛 C-H 胺化适用于醛和氟芳基叠氮化物的不同组合，产生相应的N-氟芳基酰胺的产率非常好。一系列机理研究支持 Co( II ) 催化的分子间 C-H 胺化的逐步自由基机制。

  DOI：

  10.1039/c4sc00697f

文献信息

• 2-Arylbenzoxazole formation through o-fluoro displacement reactions
  作者：Robert J. Perry、B. David Wilson

  DOI：10.1021/jo00049a057

  日期：1992.11
• Antitumour properties of fluorinated benzothiazole-substituted hydroxycyclohexa-2,5-dienones (‘quinols’)
  作者：Cedric J. Lion、Charles S. Matthews、Geoffrey Wells、Tracey D. Bradshaw、Malcolm F.G. Stevens、Andrew D. Westwell

  DOI：10.1016/j.bmcl.2006.07.072

  日期：2006.10

  The synthesis and in vitro antitumour evaluation of a new series of fluorinated benzothiazole-substituted 4-hydroxycyclohexa-2,5-dienones ('quinols') is described. The new compounds were found to be of comparable activity compared to the nonfluorinated precursor PMX 464, in terms of antiproliferative activity in sensitive human cancer cell lines (nanomolar GI(50) values) and inhibitory activity against the thioredoxin signalling system. (c) 2006 Elsevier Ltd. All rights reserved.
• Selective radical amination of aldehydic C(sp²)–H bonds with fluoroaryl azides via Co(<scp>ii</scp>)-based metalloradical catalysis: synthesis of N-fluoroaryl amides from aldehydes under neutral and nonoxidative conditions
  作者：Li-Mei Jin、Hongjian Lu、Yuan Cui、Christopher L. Lizardi、Thiago N. Arzua、Lukasz Wojtas、Xin Cui、X. Peter Zhang

  DOI：10.1039/c4sc00697f

  日期：——

  proven to be an effective metalloradical catalyst for intermolecular amination of C(sp2)–H bonds of aldehydes with fluoroaryl azides. The [Co(P1)]-catalyzed process can employ aldehydes as the limiting reagents and operate under neutral and nonoxidative conditions, generating nitrogen gas as the only byproduct. The metalloradical aldehydic C–H amination is suitable for different combinations of aldehydes

  D 2h对称酰胺卟啉 3,5-Di t Bu-IbuPhyrin [Co( P1 )]的 Co( II ) 配合物已被证明是一种有效的金属基催化剂，用于 C(sp 2 )–H 键的分子间胺化醛与氟芳基叠氮化物。[Co( P1 )]-催化过程可以使用醛作为限制试剂并在中性和非氧化条件下运行，产生氮气作为唯一的副产品。金属基醛 C-H 胺化适用于醛和氟芳基叠氮化物的不同组合，产生相应的N-氟芳基酰胺的产率非常好。一系列机理研究支持 Co( II ) 催化的分子间 C-H 胺化的逐步自由基机制。
• 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.