3-氯-5-硝基水杨基苯胺 | 6505-75-5

• 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: 3-氯-5-硝基水杨基苯胺
• 英文名称: N-(3-chlorophenyl)-2-hydroxy-5-nitrobenzamide
• 英文别名: 2-hydroxy-5-nitro-benzoic acid-(3-chloro-anilide)；2-Hydroxy-5-nitro-benzoesaeure-(3-chlor-anilid)；Salicylanilide, 3'-chloro-5-nitro-
• CAS: 6505-75-5
• 化学式: C₁₃H₉ClN₂O₄
• 分子量: 292.678
• InChiKey: IQYMVVCMLCXPEU-UHFFFAOYSA-N

物化性质

• 沸点：
  407.2±45.0 °C(Predicted)
• 密度：
  1.4587 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  3-氯-5-硝基水杨基苯胺 在 镍 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 生成 5-amino-N-(3-chlorophenyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Acryloylamino-salicylanilides as EGFR PTK inhibitors

  摘要：

  A series of acryloylamino-salicylanilides were synthesized as inhibitors of EGFR PTK. A strategy of pseudo six-membered ring formed through intramolecular hydrogen bonding in salicylanilides is employed to mimic the planar pyrimidine ring of quinazoline EGFR inhibitors. Acrylamido moiety is incorporated to target the Cys-773 of EGFR specifically. Some of the obtained compounds exhibited good activity as EGFR inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.088
• 作为产物：
  描述：

  5-硝基水杨酸 、 3-氯苯胺 在 三氯化磷 作用下， 以76%的产率得到3-氯-5-硝基水杨基苯胺
  参考文献：
  名称：

  Novel derivatives of nitro-substituted salicylic acids: Synthesis, antimicrobial activity and cytotoxicity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.10.029

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.
• Acryloylamino-salicylanilides as EGFR PTK inhibitors
  作者：Wei Deng、Zongru Guo、Yanshen Guo、Zhiqiang Feng、Yi Jiang、Fengming Chu

  DOI：10.1016/j.bmcl.2005.06.088

  日期：2006.1

  A series of acryloylamino-salicylanilides were synthesized as inhibitors of EGFR PTK. A strategy of pseudo six-membered ring formed through intramolecular hydrogen bonding in salicylanilides is employed to mimic the planar pyrimidine ring of quinazoline EGFR inhibitors. Acrylamido moiety is incorporated to target the Cys-773 of EGFR specifically. Some of the obtained compounds exhibited good activity as EGFR inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.