1,3-di((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-benzimidazol-3-ium chloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1,3-di((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-benzimidazol-3-ium chloride
• 英文别名: (benzo[d]1,2,3-triazole-1-yl)methyl；1-[[3-(Benzotriazol-1-ylmethyl)benzimidazol-1-ium-1-yl]methyl]benzotriazole;chloride；1-[[3-(benzotriazol-1-ylmethyl)benzimidazol-1-ium-1-yl]methyl]benzotriazole;chloride
• 化学式: C₂₁H₁₇N₈*Cl
• 分子量: 416.873
• InChiKey: QOJQKMRAXOPHJQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-di((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-benzimidazol-3-ium chloride 、 silver(l) oxide 以 二氯甲烷 为溶剂， 反应 24.0h， 以38%的产率得到bis[1,3-bis((1H-benzo[d]1,2,3-triazole-1-yl)methyl)benzimidazole-2-ylidene]silver(I) dichloro argentate(I)
  参考文献：
  名称：

  Benzotriazole functionalized N-heterocyclic carbene–silver(I) complexes: Synthesis, cytotoxicity, antimicrobial, DNA binding, and molecular docking studies

  摘要：

  In this study, six [Ag(NHC)(2)](+)[AgCl2](-) type silver complexes were synthesized by the reaction of corresponding carbene precursor and Ag2O. One [Ag(NHC)(2)]+NO3- type complex was synthesized by the anion exchange reaction of corresponding silver-NHC and NaNO3. The synthesized complexes were characterized by H-1 NMR, C-13 NMR and IR spectroscopic methods, and elemental analysis. X-ray crystal structure of 5a was also reported. Cytotoxicities of all compounds were evaluated against human breast (MCF-7) and colorectal (Caco-2) cancer cell lines and non-cancer mouse fibroblast (L-929) cell lines. All complexes performed stronger activity against both cancer cell lines than standard compound cisplatin while complex 3b performed nearly equal cytotoxicity to cisplatin against non-cancer L-929. Antimicrobial effects of all compounds were evaluated against Escherichia coli, Bacillus subtilis and Candida albicans and good activities were observed. The docking results indicated that complex 3b might be classified as druggable molecule in drug design. DNA binding study also demonstrates that 3b complex has an interaction ability to DNA. Combination of experimental and molecular docking results revealed that reported complexes are promising structures and deserve further research as anticancer drugs. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.06.052
• 作为产物：
  描述：

  1-(氯甲基)-1H-苯并三唑 在 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 1,3-di((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-benzimidazol-3-ium chloride
  参考文献：
  名称：

  功能化的咪唑鎓和苯并咪唑鎓盐作为对氧磷酶1抑制剂：合成，表征和分子对接研究

  摘要：

  对氧磷酶（PON）是活生物体代谢中的关键酶，PON1活性下降被认为是动脉粥样硬化和有机磷酸酯毒性的风险。本研究描述了功能化的咪唑鎓盐和苯并咪唑鎓盐（1a – 5g）的合成，表征，PON1抑制特性和分子对接研究。通过IR，NMR，元素分析来阐明所有化合物的结构，并通过单晶X射线衍射表征化合物2b和2c的结构。香豆素取代的咪唑鎓盐化合物1c对PON1的活性表现出最佳的抑制作用，IC 50良好值（6.37μM）。对该化合物的动力学研究进行了评估，结果表明该化合物是PON1的竞争性抑制剂，K i值为2.39μM。还对大多数活性化合物1c和最小活性化合物2c进行了分子对接研究，以确定可能的PON1活性位点结合模型并验证了实验结果。

  DOI：

  10.1016/j.bmc.2016.02.012

文献信息

• Functionalized imidazolium and benzimidazolium salts as paraoxonase 1 inhibitors: Synthesis, characterization and molecular docking studies
  作者：Mert Olgun Karataş、Harun Uslu、Bülent Alıcı、Başak Gökçe、Nahit Gencer、Oktay Arslan、N. Burcu Arslan、Namık Özdemir

  DOI：10.1016/j.bmc.2016.02.012

  日期：2016.3

  acknowledged as a risk for atherosclerosis and organophosphate toxicity. The present study describes the synthesis, characterization, PON1 inhibitory properties and molecular docking studies of functionalized imidazolium and benzimidazolium salts (1a–5g). The structures of all compounds were elucidated by IR, NMR, elemental analysis and structures of compounds 2b and 2c were characterized by single-crystal

  对氧磷酶（PON）是活生物体代谢中的关键酶，PON1活性下降被认为是动脉粥样硬化和有机磷酸酯毒性的风险。本研究描述了功能化的咪唑鎓盐和苯并咪唑鎓盐（1a – 5g）的合成，表征，PON1抑制特性和分子对接研究。通过IR，NMR，元素分析来阐明所有化合物的结构，并通过单晶X射线衍射表征化合物2b和2c的结构。香豆素取代的咪唑鎓盐化合物1c对PON1的活性表现出最佳的抑制作用，IC 50良好值（6.37μM）。对该化合物的动力学研究进行了评估，结果表明该化合物是PON1的竞争性抑制剂，K i值为2.39μM。还对大多数活性化合物1c和最小活性化合物2c进行了分子对接研究，以确定可能的PON1活性位点结合模型并验证了实验结果。
• Benzotriazole functionalized N-heterocyclic carbene–silver(I) complexes: Synthesis, cytotoxicity, antimicrobial, DNA binding, and molecular docking studies
  作者：Gülnihan Onar、Mert Olgun Karataş、Sevgi Balcıoğlu、Tuğba Taşkın Tok、Canbolat Gürses、Işın Kılıç-Cıkla、Namık Özdemir、Burhan Ateş、Bülent Alıcı

  DOI：10.1016/j.poly.2018.06.052

  日期：2018.10

  In this study, six [Ag(NHC)(2)](+)[AgCl2](-) type silver complexes were synthesized by the reaction of corresponding carbene precursor and Ag2O. One [Ag(NHC)(2)]+NO3- type complex was synthesized by the anion exchange reaction of corresponding silver-NHC and NaNO3. The synthesized complexes were characterized by H-1 NMR, C-13 NMR and IR spectroscopic methods, and elemental analysis. X-ray crystal structure of 5a was also reported. Cytotoxicities of all compounds were evaluated against human breast (MCF-7) and colorectal (Caco-2) cancer cell lines and non-cancer mouse fibroblast (L-929) cell lines. All complexes performed stronger activity against both cancer cell lines than standard compound cisplatin while complex 3b performed nearly equal cytotoxicity to cisplatin against non-cancer L-929. Antimicrobial effects of all compounds were evaluated against Escherichia coli, Bacillus subtilis and Candida albicans and good activities were observed. The docking results indicated that complex 3b might be classified as druggable molecule in drug design. DNA binding study also demonstrates that 3b complex has an interaction ability to DNA. Combination of experimental and molecular docking results revealed that reported complexes are promising structures and deserve further research as anticancer drugs. (C) 2018 Elsevier Ltd. All rights reserved.