1-(4-nitrophenyl)aminobenzimidazole | 185012-05-9

• 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: 1-(4-nitrophenyl)aminobenzimidazole
• 英文别名: N-(4-nitrophenyl)benzimidazol-1-amine
• CAS: 185012-05-9
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: JVGHDOMLPKJTNN-UHFFFAOYSA-N

物化性质

• 沸点：
  465.8±47.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)aminobenzimidazole 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 4.5h， 生成 N-甲基对硝基苯胺
  参考文献：
  名称：

  1-（硝基苯基）-氨基苯并咪唑的一些性质

  摘要：

  DOI：

  10.1007/bf02256841
• 作为产物：
  描述：

  1-methyl-3-(4-nitrophenylamino)benzimidazolium iodide 在 水 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以10.4%的产率得到1-(4-nitrophenyl)aminobenzimidazole
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724

文献信息

• N-arylation of 1-aminobenzimidazole
  作者：A. F. Pozharskii、O. V. Dyablo、V. V. Kuz'menko、E. A. Evgrafova

  DOI：10.1007/bf01169226

  日期：1996.10
• Some properties of 1-(nitrophenyl)-aminobenzimidazoles
  作者：O. V. Dyablo、A. F. Pozharskii、N. N. Shkurupii

  DOI：10.1007/bf02256841

  日期：2000.1
• Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt
  作者：Toyo Kaiya、Tomoko Fujiwara、Kohfuku Kohda

  DOI：10.1021/tx0000724

  日期：2000.10.1

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.