3-nitro-N-[2-[(3-nitrobenzoyl)amino]-4-methoxyphenyl]benzamide | 1254103-70-2

• 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: 3-nitro-N-[2-[(3-nitrobenzoyl)amino]-4-methoxyphenyl]benzamide
• 英文别名: N-[4-methoxy-2-[(3-nitrobenzoyl)amino]phenyl]-3-nitrobenzamide
• CAS: 1254103-70-2
• 化学式: C₂₁H₁₆N₄O₇
• 分子量: 436.381
• InChiKey: DZVRFHKAYWKWNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-nitro-N-[2-[(3-nitrobenzoyl)amino]-4-methoxyphenyl]benzamide 在 10% palladium on activated carbon 、 氢气 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 对二甲苯 、 乙酸乙酯 、 乙腈 为溶剂， 反应 24.0h， 生成 tert-butyl 2-(3-aminophenyl)-5-methoxy-1H-benzo[d]imidazole-1-carboxylate
  参考文献：
  名称：

  Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against Chlamydia pneumoniae

  摘要：

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

  DOI：

  10.1021/jm1008083
• 作为产物：
  描述：

  2-硝基-4-甲氧基苯胺 在 吡啶 、 4-二甲氨基吡啶 、 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 5.25h， 生成 3-nitro-N-[2-[(3-nitrobenzoyl)amino]-4-methoxyphenyl]benzamide
  参考文献：
  名称：

  Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against Chlamydia pneumoniae

  摘要：

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.

  DOI：

  10.1021/jm1008083

文献信息

• Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against <i>Chlamydia pneumoniae</i>
  作者：Leena Keurulainen、Olli Salin、Antti Siiskonen、Jan Marco Kern、Joni Alvesalo、Paula Kiuru、Matthias Maass、Jari Yli-Kauhaluoma、Pia Vuorela

  DOI：10.1021/jm1008083

  日期：2010.11.11

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.