2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one | 221121-30-8

• 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-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one
• 英文别名: 2-(4-Fluorophenyl)-1-imidazol-1-ylethanone
• CAS: 221121-30-8
• 化学式: C₁₁H₉FN₂O
• 分子量: 204.204
• InChiKey: QDFRVSPLXHZUKM-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±44.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one 在 sodium ethanolate 、 potassium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 2-sec-Butylsulfanyl-6-(4-fluoro-benzyl)-5-methyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  5-Alkyl-2-(alkylthio)-6-(2,6-dihalophenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones:  Novel Potent and Selective Dihydro-alkoxy-benzyl-oxopyrimidine Derivatives

  摘要：

  Molecular modeling analysis of compounds belonging to the recently published series of dihydroalkoxy-benzyl-oxopyrimidines (DABOs), such as S-DABOs and DATNOs, gave support to the design of new 2,6-disubstituted benzyl-DABO derivatives as highly potent and specific inhibitors of the HIV-1 reverse transcriptase (RT). To follow up on the novel DABO derivatives, we decided to investigate the effect of electron-withdrawing substituents in the benzyl unit of the S-DABO skeleton versus their anti-HIV-1 activity. Such chemical modifications impacted the inhibitory activity, especially when two halogen units were introduced at positions 2 and 6 in the phenyl portion of the benzyl group bound to C-6 of the pyrimidine ring. Various 5-alkyl-2-(alkyl(or cycloalkyl)thio)-6-(2,B-dichloro(or 2, 6-difluoro)phenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones were then synthesized and tested as anti-HIV-1 agents in both cell-based and enzyme (recombinant reverse transcriptase, rRT) assays. Among the various mono- and disubstituted phenyl derivatives, the most potent were those containing a 6-(2,6-difluorophenylmethyl) substituent (F-DABOs), which showed EC50's ranging between 40 and 90 nM and selectivity indexes up to greater than or equal to 5000. An excellent correlation was found between EC50 and IC50 values which confirmed that these compounds act as inhibitors of the HIV-1 RT. The structure-activity relationships of the newly synthesized pyrimidinones are presented herein.

  DOI：

  10.1021/jm980260f
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 4-氟苯乙酸 以 乙腈 为溶剂， 生成 2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one
  参考文献：
  名称：

  具有亚纳摩尔级抗HIV-1活性的新S-DABO衍生物的平行溶液相和微波辅助合成。

  摘要：

  已经建立了用于平行溶液相合成的简单而有效的方法，以获得一系列硫尿嘧啶，然后在微波辐射下选择性地将S-苄基化，得到新的S-DABO。生物筛选导致鉴定出对高度纯化的重组人免疫缺陷病毒1型（HIV-1）逆转录酶（RT）酶（野生型和突变型）和野生型（wt）和突变型HIV具有纳摩尔活性的化合物-1株。特别是，发现20种是迄今为止报道的最有效的S-DABO（针对分离的wt酶的ID50 = 26 nM），对wt和多抗性病毒（IRLL98）HIV-1菌株均具有亚纳摩尔活性（EC50 <0.14 nM和EC50分别为0.22 nM）。

  DOI：

  10.1021/jm050744t

文献信息

• Exploiting the Imidazolium Effect in Base-free Ammonium Enolate Generation: Synthetic and Mechanistic Studies
  作者：Claire M. Young、Daniel G. Stark、Thomas H. West、James E. Taylor、Andrew D. Smith

  DOI：10.1002/anie.201608046

  日期：2016.11.7

  function as ammonium enolate precursors in the absence of base. Enantioselective Michael addition–cyclization reactions using different α,β‐unsaturated Michael acceptors have been performed to form dihydropyranones and dihydropyridinones with high stereoselectivity. Detailed mechanistic studies using RPKA have revealed the importance of the “imidazolium” effect in ammonium enolate formation and have highlighted

  在没有碱的情况下，N-酰基咪唑和催化的异硫脲盐酸盐催化物起烯醇铵的前体作用。已经进行了使用不同的α，β-不饱和Michael受体的对映选择性Michael加成环化反应，以形成具有高立体选择性的二氢吡喃酮和二氢吡啶并酮。使用RPKA进行的详细机械研究揭示了“咪唑”效应在烯醇铵形成中的重要性，并强调了与传统碱介导方法的主要区别。
• 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。
• 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。
• N → N’ acyl migration in the context of a medicinal chemistry program
  作者：Dennis Anderson、Guoyun Bai、Shawn Cabral、David W. Piotrowski、Liuqing Wei

  DOI：10.1016/j.tet.2022.132950

  日期：2022.9

  A series of tertiary amides was identified as lead matter for a new medicinal chemistry program. Analysis of analogs made for structure activity studies and physicochemical property measurements revealed that some of these tertiary amides were prone to acyl migration. A series of compounds designed to assess the propensity for acyl migration was synthesized. Qualitative time and temperature kinetics

  一系列叔酰胺被确定为新药物化学计划的铅物质。对用于结构活性研究和物理化学性质测量的类似物的分析表明，这些叔酰胺中的一些易于发生酰基迁移。合成了一系列旨在评估酰基迁移倾向的化合物。使用1 H NMR 技术对定性时间和温度动力学进行定量动力学测量。该系列中的许多经过检查的叔酰胺显示在 pH 值和温度范围内迁移。我们的发现为其他使用类似性质的酰胺的人提供了警示。
• New Tetracyclic Derivatives of Imidazo[1,5-a][1,4]benzodiazepines and of Imidazo[1,5-a]-thieno[3,2-f][1,4]-diazepines
  作者：Max Gerecke、Emilio Kyburz、René Boner、Walter Gassner

  DOI：10.3987/com-94-s(b)61

  日期：——

  The synthesis of new tetracyclic 1,4-diazepine derivatives is described. In these compounds, an additional five-membered heterocycle is fused on the known tricyclic ring systems imidazo[1,5-a][1,4]benzodiazepine and imidazo[1,5-a]thieno[3,2-f][1,4]diazepine. Many of these new compounds display a very high affinity to the benzodiazepine receptor in mammals.