2-(4-methoxy-3-nitrophenyl)benzimidazole | 340828-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-methoxy-3-nitrophenyl)benzimidazole
• 英文别名: 2-(4-methoxy-3-nitrophenyl)-1H-benzimidazole
• CAS: 340828-78-6
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: QPPUHIBXHDDVBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-3-nitrophenyl)benzimidazole 在 草酰氯 、 氯化铵 、 锌 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 3.0h， 生成 N-(5-(benzimidazol-2-yl)-2-methoxyphenyl)but-2-yneamide
  参考文献：
  名称：

  含苯并咪唑环丙炔酰胺类衍生物及其制法和 药物组合物与用途

  摘要：

  本发明涉及式I所示的含苯并咪唑环丙炔酰胺类衍生物，其可药用盐，及其制备方法，含有一个或多个这化合物的组合物，和该类化合物在治疗肿瘤疾病方面的用途。

  公开号：

  CN105085406B
• 作为产物：
  描述：

  4-甲氧基-3-硝基苯甲酸 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 对二甲苯 为溶剂， 反应 19.75h， 生成 2-(4-methoxy-3-nitrophenyl)benzimidazole
  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

• Synthesis, characterization, and antimicrobial screening of some Mannich base sydnone derivatives
  作者：Piyush P. Savaliya、Vikunjana K. Akbari、Jigisha A. Modi、Keshav C. Patel

  DOI：10.1007/s00044-013-0568-6

  日期：2013.12

  The title compounds (5a-j), (6a-j), and (7a-j) were prepared via a four-step procedure using starting material 4-methoxyaniline (1). The structure of all synthesized compounds was confirmed by FT-IR, H-1 NMR, C-13 NMR, and CHN analysis. The synthesized compounds were tested for their antibacterial and antifungal activity (MIC) in vitro against organisms viz. B. subtilis, S. aureus, E. coli, P. aeruginosa, and C. albicans taking ciprofloxacin, ampicillin, streptomycin, penicillin-G, fluconazole, and nystatin as the standard drugs. Some of the compounds have shown significant activities.
• 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.
• 含苯并咪唑环丙炔酰胺类衍生物及其制法和 药物组合物与用途
  申请人：中国医学科学院药物研究所

  公开号：CN105085406B

  公开（公告）日：2020-11-03

  本发明涉及式I所示的含苯并咪唑环丙炔酰胺类衍生物，其可药用盐，及其制备方法，含有一个或多个这化合物的组合物，和该类化合物在治疗肿瘤疾病方面的用途。