8-hydroxy-N-(3-nitrophenyl)quinoline-2-carboxamide

• 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: 8-hydroxy-N-(3-nitrophenyl)quinoline-2-carboxamide
• 英文别名: [3-[(8-Hydroxyquinoline-2-carbonyl)amino]phenyl]azinic acid
• 化学式: C₁₆H₁₁N₃O₄
• 分子量: 309.281
• InChiKey: SNWRDRMENVWGAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-羟基喹啉-2-羧酸 、 间硝基苯胺 在 三氯化磷 作用下， 以 氯苯 为溶剂， 生成 8-hydroxy-N-(3-nitrophenyl)quinoline-2-carboxamide
  参考文献：
  名称：

  Activity of ring-substituted 8-hydroxyquinoline-2-carboxanilides against intestinal sulfate-reducing bacteria Desulfovibrio piger

  摘要：

  Desulfovibrio genus is dominant among sulfate-reducing bacteria (SRB) in the large intestine of healthy people and animals. It is mostly isolated from patients with inflammatory bowel disease (IBD) and can be involved in the disease initiation. Primary in vitro screening of 8-hydroxyquinoline-2-carboxanilides was performed against Desulfovibrio piger Vib-7 representing SRB. The most effective compounds with MIC90/MBC values in the range of 17-23 mu M/20-23 mu M, respectively, were substituted in C'((3)) by CF3, OCH3, CH3 and in C'((4)) by CF3. Their activity was twofold higher than that of ciprofloxacin. These compounds did not express any significant cytotoxic effect on THP-1 cells up to the tested concentration of 30 mu M. The antibacterial efficacy of the most active C'((3))-substituted compounds practically did not change with increasing compound lipophilicity, indicating that this position of substitution is favorable for significant antimicrobial effect, while the antibacterial activity of most of C'((2)) and C'((4))-substituted derivatives decreased linearly with increasing compound lipophilicity. In addition, the dependence of activity on electronic Hammett's sigma parameter of the substituent R was quasi-parabolic for the most effective C'((3))-substituted compounds.

  DOI：

  10.1007/s00044-017-2067-7

文献信息

• Ring-substituted 8-hydroxyquinoline-2-carboxanilides as potential antimycobacterial agents
  作者：Jiri Kos、Iveta Zadrazilova、Eoghan Nevin、Michal Soral、Tomas Gonec、Peter Kollar、Michal Oravec、Aidan Coffey、Jim O’Mahony、Tibor Liptaj、Katarina Kralova、Josef Jampilek

  DOI：10.1016/j.bmc.2015.06.047

  日期：2015.8

  In this study, a series of twenty-two ring-substituted 8-hydroxyquinoline-2-carboxanilides was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, Mycobacterium avium complex and M. avium subsp. paratuberculosis. Some of the tested compounds showed the antimycobacterial activity against M. avium subsp. paratuberculosis comparable with or higher than that of rifampicin. 8-Hydroxy-N-[3-(trifluoromethyl) phenyl]- and 8-hydroxy-N-[4-(trifluoromethyl) phenyl] quinoline-2-carboxamide showed MIC = 24 mu M against all tested mycobacterial strains. 3-Methoxyphenyl- and 3-methylphenyl derivatives expressed MIC = 27 or 29 mu M also against all the tested strains. Their activity against M. avium subsp. paratuberculosis was 4-fold higher than that of rifampicin. 2-Bromophenyl- and 2-(trifluoromethyl) phenyl derivatives had MIC = 23 or 24 mu M against M. tuberculosis. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT assay. Screening of cytotoxicity of the compounds was performed using the THP-1 cells, and no significant lethal effect was observed up to tested concentration 30 mu M. The structure-activity relationships are discussed. (C) 2015 Elsevier Ltd. All rights reserved.
• Activity of ring-substituted 8-hydroxyquinoline-2-carboxanilides against intestinal sulfate-reducing bacteria Desulfovibrio piger
  作者：Ivan Kushkevych、Jiri Kos、Peter Kollar、Katarina Kralova、Josef Jampilek

  DOI：10.1007/s00044-017-2067-7

  日期：2018.1

  Desulfovibrio genus is dominant among sulfate-reducing bacteria (SRB) in the large intestine of healthy people and animals. It is mostly isolated from patients with inflammatory bowel disease (IBD) and can be involved in the disease initiation. Primary in vitro screening of 8-hydroxyquinoline-2-carboxanilides was performed against Desulfovibrio piger Vib-7 representing SRB. The most effective compounds with MIC90/MBC values in the range of 17-23 mu M/20-23 mu M, respectively, were substituted in C'((3)) by CF3, OCH3, CH3 and in C'((4)) by CF3. Their activity was twofold higher than that of ciprofloxacin. These compounds did not express any significant cytotoxic effect on THP-1 cells up to the tested concentration of 30 mu M. The antibacterial efficacy of the most active C'((3))-substituted compounds practically did not change with increasing compound lipophilicity, indicating that this position of substitution is favorable for significant antimicrobial effect, while the antibacterial activity of most of C'((2)) and C'((4))-substituted derivatives decreased linearly with increasing compound lipophilicity. In addition, the dependence of activity on electronic Hammett's sigma parameter of the substituent R was quasi-parabolic for the most effective C'((3))-substituted compounds.