1-{[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-1H-benzo[d]imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-1H-benzo[d]imidazole
• 英文别名: 1-[[1-(2-Fluorophenyl)triazol-4-yl]methyl]benzimidazole；1-[[1-(2-fluorophenyl)triazol-4-yl]methyl]benzimidazole
• 化学式: C₁₆H₁₂FN₅
• 分子量: 293.303
• InChiKey: AABJDBIUWZVBBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并咪唑 在 铜 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 60.0~80.0 ℃ 、100.0 kPa 条件下， 反应 25.0h， 生成 1-{[1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-1H-benzo[d]imidazole
  参考文献：
  名称：

  1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity

  摘要：

  Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 and 29-30) or penciclovir-like subunit (31a,b-38a) were designed and synthesized to evaluate their antibacterial activities against selected Gram-positive and Gram-negative bacteria. Hybridization approach using environmentally friendly Cu (I)-catalyzed click reaction under microwave irradiation was adopted in the synthesis of regioselective 1,4-disubstituted 1,2,3-triazole tethered heterocycles (9-23 and 25-30), while post-N-alkylation of NH-1,2,3-triazoles afforded both 2,4-(31a-38a) and 1,4-disubstituted (31b-33b, 35b-37b) 1,2,3-triazole regioisomers. The compounds 18-23 and 25-30 revealed fluorescence in the violet region of the visible spectrum with a strong influence of phenyl spacer in 25-30 on both wavelength and emission intensity. Fusion of selected subunits led to new hybrid architecture, benzothiazole-1,2,3-triazole-coumarin 29 that demonstrated extremely narrow spectrum activity towards fastidious Gram-negative bacteria Moraxella catarrhalis. Selected hybrid showed the potency against Moraxella catarrhalis (MIC <= 0.25 mu g/mL) comparable to that of reference antibiotic azithromycin, which suggested that further investigations are necessary to optimize this potential hit compound as a new anti-Moraxella catarrhalis agent. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.042

文献信息

• Small molecule purine and pseudopurine derivatives: synthesis, cytostatic evaluations and investigation of growth inhibitory effect in non-small cell lung cancer A549
  作者：Andrea Bistrović、Petra Grbčić、Anja Harej、Mirela Sedić、Sandra Kraljević-Pavelić、Sanja Koštrun、Janez Plavec、Damjan Makuc、Silvana Raić-Malić

  DOI：10.1080/14756366.2017.1414807

  日期：2018.1.1

  Novel halogenated purines and pseudopurines with diverse aryl-substituted 1,2,3-triazoles were prepared. While p-(trifluoromethyl)-substituted 1,2,3-triazole in N-9 alkylated purine and 3-deazapurine was critical for strong albeit unselective activity on pancreatic adenocarcinoma cells CFPAC-1,1-(p-fluorophenyl)-1,2,3-triazole derivative of 7-deazapurine showed selective cytostatic effect on metastatic colon cancer cells SW620. Importantly, 1-(p-chlorophenyl)-1,2,3-triazole-tagged benzimidazole displayed the most pronounced and highly selective inhibitory effect in nM range on non-small cell lung cancer A549. This compound revealed to target molecular processes at the extracellular side and inside the plasma membrane regulated by GPLD1 and growth factor receptors PDGFR and IGF-1R leading to the inhibition of cell proliferation and induction of apoptosis mediated by p38 MAP kinase and NF-kappa B, respectively. Further optimisation of this compound as to reduce its toxicity in normal cells may lead to the development of novel agent effective against lung cancer.[GRAPHICS].