1H-Benzoimidazole-2-carboxylic acid [1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide | 107997-36-4

• 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: 1H-Benzoimidazole-2-carboxylic acid [1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide
• 英文别名: N’-(4-hydroxybenzylidene)-1H-benzoimidazole-2-carbohydrazide
• CAS: 107997-36-4
• 化学式: C₁₅H₁₂N₄O₂
• 分子量: 280.286
• InChiKey: YNMLODMDZGUOPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  21.0
• 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：
  90.37
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1H-苯并咪唑-2-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1H-Benzoimidazole-2-carboxylic acid [1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide
  参考文献：
  名称：

  Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

  摘要：

  Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.054

文献信息

• In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives
  作者：Anna Baldisserotto、Monica Demurtas、Ilaria Lampronti、Massimo Tacchini、Davide Moi、Gianfranco Balboni、Silvia Vertuani、Stefano Manfredini、Valentina Onnis

  DOI：10.3390/ph13040068

  日期：——

  activity is related to the presence of at least two hydroxy groups on arylidene moiety of benzimidazoles. Structure activity analysis revealed that the position of hydroxy groups is crucial for antioxidant activity as well as the presence of a 2-hydroxy-4-(diethylamino)arylidene group. The same correlation pattern was found to be related to photoprotective activity resulting in an UVA Protection Factor

  在寻找多功能化合物的过程中，我们设计了具有苯酚羟基和a部分作为潜在自由基清除剂和抗氧化剂的苯并咪唑衍生物。目标分子已通过简单的合成程序制备，并通过DPPH，FRAP和ORAC测试测试了其抗氧化活性，针对紫外线的光保护活性以及针对Colo-38黑色素瘤细胞的抗增殖活性。此外，制备了两种不同的皮肤美容制剂，这些化合物具有最佳的抗氧化剂和光防护特性，并使用Franz Cells系统评估了它们从制剂中的释放。高抗氧化活性与苯并咪唑的亚芳基部分上存在至少两个羟基有关。结构活性分析表明，羟基的位置对于抗氧化剂活性以及2-羟基-4-（二乙基氨基）亚芳基的存在至关重要。发现相同的相关模式与光保护活性相关，从而产生比商业日光过滤器PBSA更好的UVA保护因子和对黑素瘤细胞的抗增殖活性，而不会对正常角质形成细胞产生细胞毒性。释放分析表明，在与用作紫外线防晒过滤剂的浓度相当的情况下，在有限的释放范围内实现了高抗
• Graubaum, Heinz; Martin, Dieter, Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 4, p. 515 - 521
  作者：Graubaum, Heinz、Martin, Dieter

  DOI：——

  日期：——
• Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
  作者：Gilda Giancotti、Michela Cancellieri、Andrea Balboni、Mariateresa Giustiniano、Ettore Novellino、Leen Delang、Johan Neyts、Pieter Leyssen、Andrea Brancale、Marcella Bassetto

  DOI：10.1016/j.ejmech.2018.02.054

  日期：2018.4

  Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus. (C) 2018 Elsevier Masson SAS. All rights reserved.