2-(4-Bromophenyl)-1-imidazol-1-ylethanone | 1267766-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Bromophenyl)-1-imidazol-1-ylethanone
• 英文别名: 2-(4-bromophenyl)-1-imidazol-1-ylethanone
• CAS: 1267766-12-0
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: CIDOZPDBVKDARN-UHFFFAOYSA-N

物化性质

• 沸点：
  420.9±47.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-Bromophenyl)-1-imidazol-1-ylethanone 在 copper(l) iodide 、 1-butyl-3-methylimidazolium hexafluorophosphate 、 palladium diacetate 作用下， 反应 8.0h， 生成 4-((4-(6-methoxy-2-oxo-2H-chromen-3-yl)phenyl)ethynyl)benzonitrile
  参考文献：
  名称：

  Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes

  摘要：

  The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM] [BEd as solvent, and [PAIM][NTf (2)] as basic-IL to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151854
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 对溴苯乙酸 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 2-(4-Bromophenyl)-1-imidazol-1-ylethanone
  参考文献：
  名称：

  新型香豆素基1,2,3-三唑类化合物的微波辅助合成、生物学评价及分子对接研究

  摘要：

  采用高效、环保的方案，通过各种取代芳基叠氮化物和末端炔烃之间的铜（）催化点击反应，合成了基于香豆素的 1,4-二取代 1,2,3-三唑衍生物。与传统的加热路线相比，该合成路线易于实现，并且在微波辐射条件下具有优异的产率。所有化合物的结构均通过IR、 1 H NMR、 13 C NMR 谱和质谱进行了表征。对所有合成的化合物进行体外抗菌、抗氧化和抗炎活性筛选；在所有化合物中， 8a 、 8j 、 8k和8l相对于标准药物表现出更好的结果。此外，还使用 ​​Schrödinger 套件的 Glide 模块对 PDB ID 2VCX（抗炎）、3VXI（抗氧化剂）、4GEE（抗菌）和 2XFH（抗真菌）进行了分子对接研究。最终化合物8d 、 8e 、 8h和8k显示出与所有蛋白质中的 His-88 和 Val-191 蛋白质以及与水的最高氢键相互作用。

  DOI：

  10.1039/d0ra01052a

文献信息

• Microwave assisted synthesis of <scp>4‐methyl</scp> ‐3‐arylpyrano[2,3‐f]chromen‐2( <scp>8H</scp> )‐one derivatives, evaluation of antiproliferative, and antimicrobial activities
  作者：Ravinder Dharavath、Madderla Sarasija、Makthal Ram Reddy、Nagaraju Nalaparaju、Ramakrishna Katta、Dongamanti Ashok

  DOI：10.1002/jhet.4103

  日期：2020.11

  series of new 4‐methyl‐3‐arylpyrano[2,3‐f]chromen‐2(8H)‐one derivatives were designed and synthesized through an efficient, an eco‐friendly manner under microwave irradiation and conventional heating methods. Structures of final compounds established based on IR, NMR and mass spectral analysis. The final target compounds were screened for their in vitro antiproliferative activity by taking cisplatin as

  在微波辐射和常规加热方法下，通过高效，环保的方式设计和合成了一系列新的4-甲基-3-芳基吡喃并[2,3-f]铬n-2-（8H）-one衍生物。基于IR，NMR和质谱分析建立的最终化合物的结构。通过以顺铂为参考筛选最终的目标化合物的体外抗增殖活性，此外，通过选择诸如金黄色葡萄球菌，枯草芽孢杆菌，肺炎克雷伯菌和大肠杆菌的菌株来筛选其抗菌活性。此外，用黑曲霉，黄曲霉和尖孢镰刀菌筛选抗真菌活性。株。许多化合物具有良好的活性。
• A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity
  作者：Marina Roussaki、Christos A. Kontogiorgis、Dimitra Hadjipavlou-Litina、Stylianos Hamilakis、Anastasia Detsi

  DOI：10.1016/j.bmcl.2010.05.022

  日期：2010.7

  A series of coumarin analogues bearing a substituted phenyl ring on position 3 were synthesized via a novel methodology, through an intermolecular condensation reaction of 2-hydroxyacetophenones and 2-hydroxybenzaldehyde, with imidazolyl phenylacetic acid active intermediates. The in vitro antioxidant activity of the synthesized compounds was evaluated using two different antioxidant assays (radical scavenging ability of DPPH stable free radical and inhibition of lipid peroxidation induced by the thermal free radical AAPH). Moreover, the ability of the compounds to inhibit soybean lipoxygenase was determined as an indication of potential anti-inflammatory activity. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors
  作者：Yue-Ping Wang、Fen-Er Chen、Erik De Clercq、Jan Balzarini、Christophe Pannecouque

  DOI：10.1016/j.ejmech.2008.06.028

  日期：2009.3

  A series of new 5-alkyl-2-benzylsulfanylpyrimidin-4(3H)-ones (5a-y) bearing different substituted arylmethyl moieties at the C-6 position of the pyrimidine core have been synthesized and evaluated for their in vitro activities against HIV-1 and HIV-2 in MT-4 cell cultures. The majority of the title compounds showed moderate to good activities against HIV-1 with an IC50 range from 6.67 mu M to 0.12 mu M. Among them, 6-(3,5-dimethylbenzy]) analogue 5q exhibited the most potent anti-HIV-1 activity (IC50 = 0.12 mu M, SI > 2642), which was about 40-fold more active than the reference compounds 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine (HEPT) and 2',3'-dideoxyinosine (DDI). The structure-activity relationships (SARs) of these new congeners were further discussed. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes
  作者：Pavankumar Prabhala、Hemantkumar M. Savanur、Suraj M. Sutar、Shruti S. Malunavar、Rajesh G. Kalkhambkar、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2020.151854

  日期：2020.5

  The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM] [BEd as solvent, and [PAIM][NTf (2)] as basic-IL to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown. (C) 2020 Elsevier Ltd. All rights reserved.
• Microwave-assisted synthesis, biological evaluation and molecular docking studies of new coumarin-based 1,2,3-triazoles
  作者：Ravinder Dharavath、Nalaparaju Nagaraju、M. Ram Reddy、D. Ashok、M. Sarasija、M. Vijjulatha、Vani T、K. Jyothi、G. Prashanthi

  DOI：10.1039/d0ra01052a

  日期：——

  using a highly efficient, eco-friendly protocol via a copper(I)-catalyzed click reaction between various substituted arylazides and terminal alkynes. The synthetic route was easy to access and gave excellent yields under microwave irradiation conditions compared to the conventional heating route. The structures of all the compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and mass spectrometry

  采用高效、环保的方案，通过各种取代芳基叠氮化物和末端炔烃之间的铜（）催化点击反应，合成了基于香豆素的 1,4-二取代 1,2,3-三唑衍生物。与传统的加热路线相比，该合成路线易于实现，并且在微波辐射条件下具有优异的产率。所有化合物的结构均通过IR、 1 H NMR、 13 C NMR 谱和质谱进行了表征。对所有合成的化合物进行体外抗菌、抗氧化和抗炎活性筛选；在所有化合物中， 8a 、 8j 、 8k和8l相对于标准药物表现出更好的结果。此外，还使用 ​​Schrödinger 套件的 Glide 模块对 PDB ID 2VCX（抗炎）、3VXI（抗氧化剂）、4GEE（抗菌）和 2XFH（抗真菌）进行了分子对接研究。最终化合物8d 、 8e 、 8h和8k显示出与所有蛋白质中的 His-88 和 Val-191 蛋白质以及与水的最高氢键相互作用。