1-苄基-2-甲基-5-硝基-1H-1,3-苯并咪唑 | 14624-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-苄基-2-甲基-5-硝基-1H-1,3-苯并咪唑
• 英文名称: 1-Benzyl-2-methyl-5-nitro-1H-benzimidazole
• 英文别名: 1-benzyl-2-methyl-5-nitro-1H-benzoimidazole；N¹-Benzyl-2-methyl-5-nitro-benzimidazol；2-Methyl-1-benzyl-5-nitro-benzimidazol；5-Nitro-2-methyl-1-benzyl-benzimidazol；1-Benzyl-2-methyl-5-nitrobenzimidazol；1-benzyl-2-methyl-5-nitro-1H-1,3-benzimidazole；1-benzyl-2-methyl-5-nitrobenzimidazole
• CAS: 14624-88-5
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: DKGAUUAVZGGUIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178°

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-苄基-2-甲基-5-硝基-1H-1,3-苯并咪唑 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 1-Benzyl-5-dimethylamino-2-methyl-1H-benzimidazole
  参考文献：
  名称：

  Garuti; Giovanninetti; Ferranti, Pharmazie, 1987, vol. 42, # 6, p. 378 - 381

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯并咪唑 在 硫酸 、 硝酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 1-苄基-2-甲基-5-硝基-1H-1,3-苯并咪唑
  参考文献：
  名称：

  Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles

  摘要：

  Different substituents were introduced in position 1 of 2-methyl-5(6)-nitro-1H-benzimidazole (2) in order to obtain different side chains having different heterocyclic compounds, for example, thiadiazoles (5-7), tetrazoles (8, 9a, b), triazoles (11-13), thiazoles (14a-e), triazines (10, 16, 17), and imidazoles (18a-c). The antitumor effect of compounds 1, 2, 2a, 4, 5, 7, 8, 9a, 10, 13, 14a, 15, 16, and 18c was studied against breast cancer (MCF7) and compounds 2 [IC50 = 4.52 mu g] and 7 [IC50 = 8.29 mu g] were found to be active. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.033

文献信息

• Garuti; Ghedini; Leoni, Il Farmaco, 1993, vol. 48, # 11, p. 1531 - 1546
  作者：Garuti、Ghedini、Leoni、Baraldi、Dionisotti

  DOI：——

  日期：——
• Triazine–benzimidazole hybrids: Anticancer activity, DNA interaction and dihydrofolate reductase inhibitors
  作者：Prinka Singla、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.bmc.2015.03.012

  日期：2015.4

  A new series of triazine-benzimidazole hybrids has been synthesized with different substitution of primary and secondary amines at one of the position of triazine in moderate to good yields. These compounds were evaluated for their inhibitory activities over 60 human tumor cell lines at one dose and five dose concentrations. Compounds 6b, 8 and 9 showed broad spectrum of antitumor activities with GI(50) values of 9.79, 2.58 and 3.81 mu M, respectively. DNA binding studies also indicated strong interaction properties of these compounds. These synthesized compounds also showed inhibition of mammalian dihydrofolate reductase (DHFR). Compound 6b was depicted as the most active member of DHFR inhibitor with IC50 value of 1.05 mu M. Molecular modelling studies were used to identify the stabilized interactions of Compound 6b within the active site of enzyme for DHFR. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and inhibitory activity of new benzimidazole derivatives against Burkitt’s lymphoma promotion
  作者：Mostafa. M. Ramla、Mohamed. A. Omar、H. Tokuda、Hoda. I. El-Diwani

  DOI：10.1016/j.bmc.2007.04.010

  日期：2007.10

  As a continuation to our previous work concerning antitumor benzimidazoles, we have synthesized series of new derivatives of 2-(1-benzyl-2-methyl-1H-benzimidazol-5-ylimino)-3-(substituted)-thiazolidin-4-one (6a-e), 3-(2-methy]-1H-benzimidazol-5-yl)-2-substituted-thiazolidin-4-one (9a-f) and we have studied their inhibitory activity against the Epstein-Barr Virus-early antigen (EBV-EA) activation introduced by 12-O-tetradecanoylphorbol- 13-acetate (TPA). Compound 6d was found to be significantly active and compounds 5a and 6e were also active. (C) 2007 Elsevier Ltd. All rights reserved.
• GARUTI, L.;GIOVANNINETTI, G.;FERRANTI, A.;CHIARINI, A.;BERTOCCHI, G.;SABA+, PHARMAZIE, 42,(1987) N 6, 378-381
  作者：GARUTI, L.、GIOVANNINETTI, G.、FERRANTI, A.、CHIARINI, A.、BERTOCCHI, G.、SABA+

  DOI：——

  日期：——
• Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles
  作者：Mostafa M. Ramla、Mohamed A. Omar、Abdel-Momen M. El-Khamry、Hoda I. El-Diwani

  DOI：10.1016/j.bmc.2006.06.033

  日期：2006.11

  Different substituents were introduced in position 1 of 2-methyl-5(6)-nitro-1H-benzimidazole (2) in order to obtain different side chains having different heterocyclic compounds, for example, thiadiazoles (5-7), tetrazoles (8, 9a, b), triazoles (11-13), thiazoles (14a-e), triazines (10, 16, 17), and imidazoles (18a-c). The antitumor effect of compounds 1, 2, 2a, 4, 5, 7, 8, 9a, 10, 13, 14a, 15, 16, and 18c was studied against breast cancer (MCF7) and compounds 2 [IC50 = 4.52 mu g] and 7 [IC50 = 8.29 mu g] were found to be active. (c) 2006 Elsevier Ltd. All rights reserved.