1-(4-chlorophenyl)-2-imidazol-1-yl-ethyl 4-(4-nitrophenyl)piperazine-1-carboxylate | 1620488-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(4-chlorophenyl)-2-imidazol-1-yl-ethyl 4-(4-nitrophenyl)piperazine-1-carboxylate
• 英文别名: (±)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl 4-(4-nitrophenyl)piperazine-1-carboxylate；[1-(4-Chlorophenyl)-2-imidazol-1-yl-ethyl] 4-(4-nitrophenyl)piperazine-1-carboxylate；[1-(4-chlorophenyl)-2-imidazol-1-ylethyl] 4-(4-nitrophenyl)piperazine-1-carboxylate
• CAS: 1620488-66-5
• 化学式: C₂₂H₂₂ClN₅O₄
• 分子量: 455.901
• InChiKey: GCXOJSSBLOSPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-2-(1H-咪唑-1-基)-1-乙酮 在 甲酸 、 Noyori's catalyst 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 1-(4-chlorophenyl)-2-imidazol-1-yl-ethyl 4-(4-nitrophenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Discovery of in vitro antitubercular agents through in silico ligand-based approaches

  摘要：

  The development of new anti-tubercular agents represents a constant challenge mostly due to the insurgency of resistance to the currently available drugs. In this study, a set of 60 molecules were selected by screening the Asinex and the ZINC collections and an in house library by means of in silico ligand-based approaches. Biological assays in Mycobacterium tuberculosis H37Ra ATCC 25177 strain highlighted (+/-)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl-4-(3,4-dichlorophenyl)piperazine-1-carboxylate (5i) and 3-(4-chlorophenyl)-5-(2,4-dimethylpyrimidin-5-yl)-2-methylpyrazolo[1.5-a]pyrimidin-7(4H)-one (42) as the most potent compounds, having a Minimum Inhibitory Concentration (MIC) of 4 and 2 mu g/mL respectively. These molecules represent a good starting point for further optimization of effective anti-TB agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.05.032

文献信息

• Synthesis, biological evaluation and structure–activity correlation study of a series of imidazol-based compounds as Candida albicans inhibitors
  作者：Francesca Moraca、Daniela De Vita、Fabiana Pandolfi、Roberto Di Santo、Roberta Costi、Roberto Cirilli、Felicia Diodata D’Auria、Simona Panella、Anna Teresa Palamara、Giovanna Simonetti、Maurizio Botta、Luigi Scipione

  DOI：10.1016/j.ejmech.2014.07.001

  日期：2014.8

  against different fungal species. The biological results show that the most active compounds possess an antifungal activity comparable or higher than Fluconazole against Candida albicans, non-albicans Candida species, Cryptococcus neoformans and dermathophytes. Because of their racemic nature, the most active compounds 5f and 6c were tested as pure enantiomers. For 6c the (R)-enantiomer resulted more

  合成了一系列新的2-（1H-咪唑-1-基）-1-苯基乙醇衍生物。在体外评估了针对不同真菌种类的抗真菌活性。生物学结果表明，最具活性的化合物具有与氟康唑相当或更高的抗白色念珠菌，非白色念珠菌念珠菌，新隐球菌和皮肤真菌的抗真菌活性。由于它们的外消旋性质，测试了最具活性的化合物5f和6c为纯对映体。对于6c，（R）-对映体比（S）-1具有更高的活性，否则对于5f，（S）-对映体最活跃。为了合理化实验数据，进行了基于配体的计算研究。建模研究的结果表明（小号） - 5F和（- [R ）- 6c中完美到基于配体的模型对齐，表现出相同的相对构型。对人肺腺癌上皮细胞（A549）的初步研究表明，6c，5e和5f具有低细胞毒性。
• In vitro screening of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives as antiprotozoal agents and docking studies on Trypanosoma cruzi CYP51
  作者：Daniela De Vita、Francesca Moraca、Claudio Zamperini、Fabiana Pandolfi、Roberto Di Santo、An Matheeussen、Louis Maes、Silvano Tortorella、Luigi Scipione

  DOI：10.1016/j.ejmech.2016.02.028

  日期：2016.5

  of many parasite protozoa, such as Trypanosoma and Leishmania species, thus representing a valuable drug target for the treatment of Kinetoplastid diseases. A set of azole-based compounds selected from an in-house compound library was in vitro screened against different human protozoan parasites. Several compounds showed selective activity against Trypanosoma cruzi, with compound 7 being the most active

  甾醇14α-脱甲基酶（CYP51）是一种参与许多寄生虫原生动物（如锥虫和利什曼原虫）的存活和致病性的关键酶，因此代表了治疗运动质体疾病的重要药物靶标。从内部化合物库中选出的一组基于唑的化合物在体外针对不同的人类原生动物寄生虫进行了筛选。几种化合物显示出对克氏锥虫的选择性活性，其中化合物7的活性最高（IC 50 = 40 nM）。考虑到此处报道的化合物与已知的CYP51抑制剂之间的结构相似性，进行了分子对接研究，以评估其与原生动物靶标的结合并合理化生物学活性数据。
• Discovery of in vitro antitubercular agents through in silico ligand-based approaches
  作者：Daniela De Vita、Fabiana Pandolfi、Roberto Cirilli、Luigi Scipione、Roberto Di Santo、Laura Friggeri、Mattia Mori、Diego Fiorucci、Giorgio Maccari、Robert Selwyne Arul Christopher、Claudio Zamperini、Valentina Pau、Alessandro De Logu、Silvano Tortorella、Maurizio Botta

  DOI：10.1016/j.ejmech.2016.05.032

  日期：2016.10

  The development of new anti-tubercular agents represents a constant challenge mostly due to the insurgency of resistance to the currently available drugs. In this study, a set of 60 molecules were selected by screening the Asinex and the ZINC collections and an in house library by means of in silico ligand-based approaches. Biological assays in Mycobacterium tuberculosis H37Ra ATCC 25177 strain highlighted (+/-)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl-4-(3,4-dichlorophenyl)piperazine-1-carboxylate (5i) and 3-(4-chlorophenyl)-5-(2,4-dimethylpyrimidin-5-yl)-2-methylpyrazolo[1.5-a]pyrimidin-7(4H)-one (42) as the most potent compounds, having a Minimum Inhibitory Concentration (MIC) of 4 and 2 mu g/mL respectively. These molecules represent a good starting point for further optimization of effective anti-TB agents. (C) 2016 Elsevier Masson SAS. All rights reserved.