N-(3-fluorophenyl)-2-hydroxy-5-nitrobenzamide | 73454-93-0

• 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: N-(3-fluorophenyl)-2-hydroxy-5-nitrobenzamide
• CAS: 73454-93-0
• 化学式: C₁₃H₉FN₂O₄
• 分子量: 276.224
• InChiKey: HVNHHWGAEYYFRB-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±42.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-fluorophenyl)-2-hydroxy-5-nitrobenzamide 在 盐酸羟胺 、 铁粉 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 N-(3-fluorophenyl)-2-hydroxy-5-(7-hydroxyamino-7-oxoheptanamido) benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-aryl salicylamides with a hydroxamic acid moiety at 5-position as novel HDAC–EGFR dual inhibitors

  摘要：

  A novel series of N-aryl salicylamides with a hydroxamic acid moiety at 5-position were synthesized efficiently. Their activities against EGFR kinase and HDACs were evaluated. All compounds displayed inhibitory activity against EGFR and HDACs. The antiproliferative activities of synthesized compounds were evaluated by MTT method against human cancer cell lines A431, A549 and HL-60. Compound 1o showed the most potent inhibitory activity against A431 and A549. Compounds 1k and 1n exhibited higher potency against HL-60 than gefitinib and SAHA. N-Aryl salicylamides with a hydroxamic acid moiety at 5-position is another new HDAC-EGFR dual inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.034
• 作为产物：
  描述：

  3-氟苯胺 、 5-硝基水杨酸 在 亚磷酸三苯酯 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以94%的产率得到N-(3-fluorophenyl)-2-hydroxy-5-nitrobenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-aryl salicylamides with a hydroxamic acid moiety at 5-position as novel HDAC–EGFR dual inhibitors

  摘要：

  A novel series of N-aryl salicylamides with a hydroxamic acid moiety at 5-position were synthesized efficiently. Their activities against EGFR kinase and HDACs were evaluated. All compounds displayed inhibitory activity against EGFR and HDACs. The antiproliferative activities of synthesized compounds were evaluated by MTT method against human cancer cell lines A431, A549 and HL-60. Compound 1o showed the most potent inhibitory activity against A431 and A549. Compounds 1k and 1n exhibited higher potency against HL-60 than gefitinib and SAHA. N-Aryl salicylamides with a hydroxamic acid moiety at 5-position is another new HDAC-EGFR dual inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.034

文献信息

• Novel derivatives of nitro-substituted salicylic acids: Synthesis, antimicrobial activity and cytotoxicity
  作者：Georgios Paraskevopoulos、Martin Krátký、Jana Mandíková、František Trejtnar、Jiřina Stolaříková、Petr Pávek、Gurdyal Besra、Jarmila Vinšová

  DOI：10.1016/j.bmc.2015.10.029

  日期：2015.11

  Inspired by the high antituberculous activity of novel nitro-substituted derivatives and based on promising predicted ADMET properties we have synthesized a series of 33 salicylanilides containing nitro-group in their salicylic part and evaluated them for their in vitro antimycobacterial, antimicrobial and antifungal activities. The presence of nitro-group in position 4 of the salicylic acid was found to be beneficial and the resulting molecules exhibited minimum inhibitory concentrations (MICs) ranging from 2 to 32 mu M against Mycobacterium tuberculosis. The best activity was found for 2-hydroxy-4-nitro-N-[4-(trifluoromethyl)phenyl] benzamide (MIC = 2 mu M). 4-Nitrosalicylanilides were also found to be active against all Staphylococcus species tested while for MRSA strain 2-hydroxy-4-nitro-N-[4-(trifluoromethyl)phenyl] benzamide's MIC was 0.98 mu M. None of the nitrosalicylanilides was active against Enterococcus sp. J 14365/08 and no considerable activity was found against Gram-negative bacteria or fungi. The hepatotoxicity of all nitrosalicylanilides was found to be in the range of their MICs for HepG2 cells. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of N-aryl salicylamides with a hydroxamic acid moiety at 5-position as novel HDAC–EGFR dual inhibitors
  作者：Miao Zuo、Yue-Wen Zheng、She-Min Lu、Yan Li、San-Qi Zhang

  DOI：10.1016/j.bmc.2012.05.034

  日期：2012.7

  A novel series of N-aryl salicylamides with a hydroxamic acid moiety at 5-position were synthesized efficiently. Their activities against EGFR kinase and HDACs were evaluated. All compounds displayed inhibitory activity against EGFR and HDACs. The antiproliferative activities of synthesized compounds were evaluated by MTT method against human cancer cell lines A431, A549 and HL-60. Compound 1o showed the most potent inhibitory activity against A431 and A549. Compounds 1k and 1n exhibited higher potency against HL-60 than gefitinib and SAHA. N-Aryl salicylamides with a hydroxamic acid moiety at 5-position is another new HDAC-EGFR dual inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.