1-(2-thienyl)-2-(4-fluorophenylazo)-4,4,4-trifluorobutane-1,3-dione | 1428946-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-thienyl)-2-(4-fluorophenylazo)-4,4,4-trifluorobutane-1,3-dione
• 英文别名: 1-(thien-2-yl)-2-(p-fluorophenyldiazo)-4,4,4-trifluorobutane-1,3-dione；4,4,4-Trifluoro-2-[(4-fluorophenyl)diazenyl]-1-thiophen-2-ylbutane-1,3-dione；4,4,4-trifluoro-2-[(4-fluorophenyl)diazenyl]-1-thiophen-2-ylbutane-1,3-dione
• CAS: 1428946-70-6
• 化学式: C₁₄H₈F₄N₂O₂S
• 分子量: 344.289
• InChiKey: AYINARCLDIFDJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-thienyl)-2-(4-fluorophenylazo)-4,4,4-trifluorobutane-1,3-dione 在 硫酸 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 乙酸酐 为溶剂， 反应 8.0h， 生成 3-(2-thienyl)-4-(4-fluorophenylazo)-5-trifluoromethylisoxazole
  参考文献：
  名称：

  合成和3-（2-噻吩基）的抗微生物活性-4-芳基偶氮基-5-羟基-5-三氟甲基- Δ 2个-isoxazolines和3-（2-噻吩基）-4-芳基偶氮-5- trifluoromethylisoxazoles

  摘要：

  通过芳基重氮盐2与1-（2-噻吩基）-4,4,4-缩合制得的1-（2-噻吩基）-2-芳基偶氮-4,4,4-三氟丁烷-1,3-二酮4三氟甲基-1,3-丁二酮3，与盐酸羟胺处理，得到3-（2-噻吩基）-4-芳基偶氮基-5-羟基-5-三氟甲基- Δ 2 -isoxazolines 5。随后，5-羟基-5-三氟甲基- Δ的脱水2 -isoxazolines 5到相应的3-（2-噻吩基）-4-芳基偶氮-5- trifluoromethylisoxazoles 6通过用乙酸酐或EtOH-H处理它们来实现2 SO 4。化合物的结构是根据IR，NMR（1 H，13 C和19 F），质谱研究和元素分析。筛选了所有化合物的对四种病原细菌菌株的体外抗菌活性，这些菌株如枯草芽孢杆菌，金黄色葡萄球菌（革兰氏阳性），荧光假单胞菌，大肠杆菌（革兰氏阴性）和对两种病原真菌菌株的体外抗真菌活性。 。念珠菌，酿酒酵母;。大多

  DOI：

  10.1016/j.jfluchem.2012.10.005
• 作为产物：
  描述：

  2-噻吩甲酰三氟丙酮 、 4-氟苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 生成 1-(2-thienyl)-2-(4-fluorophenylazo)-4,4,4-trifluorobutane-1,3-dione
  参考文献：
  名称：

  4-芳基偶氮-1-苯基-3-（2-噻吩基）-5-羟基-5-三氟甲基吡唑啉和区域异构体4-芳基偶氮-1-苯基-5（3）-的合成，表征，体外DNA光裂解和细胞毒性研究（2-噻吩基）-3（5）-三氟甲基吡唑

  摘要：

  1-（2-噻吩基）-2-芳基偶氮-4,4,4-三氟丁烷-1,3-二酮（4），是由芳基重氮盐（2）与4,4,4-三氟-1-缩合生成的（2-噻吩基）丁烷-1,3-二酮（3）用作常见的中间体，以合成区域异构的4-芳基偶氮-1-苯基-5（3）-（2-噻吩基）-3（5）-三氟甲基吡唑（5和6）和4-芳基偶氮-1-苯基-3-（2-噻吩基）-5-羟基-5-三氟甲基吡唑啉（7）通过在中性条件下与苯肼反应。所有合成的化合物4，5，6和7在没有任何添加剂的情况下，在λmax 312 nm的紫外线辐射下，筛选pBR322超螺旋DNA质粒的DNA光裂解活性。结果表明3-三氟甲基异构体（5）比相应的5-三氟甲基吡唑（6）和5-羟基5-三氟甲基吡唑啉（7）更好地裂解质粒DNA 。4-（4-硝基苯基偶氮）-1-苯基-5-（2-噻吩基）-3-三氟甲基吡唑5g，显示了作为DNA光切割机的最佳潜力，将超螺旋质粒（Form-I

  DOI：

  10.1016/j.jfluchem.2020.109573

文献信息

• 4-Fluorophenylhydrazones as potential COX-2 inhibitors: a novel, efficient, one pot solid phase synthesis, docking study and pharmacological evaluation
  作者：Vinod Kumar、Girish Kumar Gupta、Kamalneet Kaur、Randhir Singh

  DOI：10.1007/s00044-013-0566-8

  日期：2013.12

  In search of a new class of organic compounds as potential COX-2 inhibitors, various 4-Fluorophenylhydrazones (3a-3i) have been synthesized and molecular docking study was conducted. All the synthesized compounds were also evaluated for their in vivo anti-inflammatory potential using carrageenan-induced rat paw odema method. In the present manuscript, a novel, simple, and greener protocol has been developed for the first time to prepare the hydrazo compounds by a one pot solid phase reaction between various active methylene compounds and p-fluoroaniline in the presence of p-toluene sulfonic acid as a new solid phase organocatalyst. The catalyst dramatically facilitates the reaction under solvent-free condition at moderate temperature (10-15 A degrees C). The present protocol not only provides an expeditious route to prepare hydrazo compounds in excellent yields (with in 3-5 min) but also avoids the use of two step conventional methods, and formation of side products. The results obtained from in vivo anti-inflammatory activity through carrageenan-induced rat paw odema assay showed that compounds 3a-3b, and 3d displayed excellent level of activity which was further supported by molecular docking study. A cyclooxygenase-II inhibitory molecular docking study has been carried out using (pdb: 1CX2) via Molegro Virtual Docker version 4.2.1. All the compounds were found to exhibit good level of inhibition and binding in the enzyme active site. Compounds 3a-3b, 3d, and 3e have been found to display high moldock scores -118.333, -118.778, -118.422, and -111.13, respectively, and are strongly bound with Arg120, Tyr355, His90, and Arg513 amino acids, which are responsible for COX-2 inhibition within the active site. In the present investigation, it can be concluded that the best scored inhibitors with good in vivo anti-inflammtory activity will have better chances to be used as anti-inflammatory leads.
• Synthesis and antimicrobial activity of 3-(2-thienyl)-4-arylazo-5-hydroxy-5-trifluoromethyl-Δ2-isoxazolines and 3-(2-thienyl)-4-arylazo-5-trifluoromethylisoxazoles
  作者：Ranjana Aggarwal、Anshul Bansal、Arpana Mittal

  DOI：10.1016/j.jfluchem.2012.10.005

  日期：2013.1

  antibacterial activity against four pathogenic bacterial strains such as Bacillus subtilis, Staphylococcus aureus (Gram-positive), Pseudomonas fluorescens, Escherichia coli (Gram-negative) and in vitro antifungal activity against two pathogenic fungal strains namely, Candida strain, Saccharomyces cerevisiae. Most of the compounds showed moderate to significant antibacterial activity selectively against

  通过芳基重氮盐2与1-（2-噻吩基）-4,4,4-缩合制得的1-（2-噻吩基）-2-芳基偶氮-4,4,4-三氟丁烷-1,3-二酮4三氟甲基-1,3-丁二酮3，与盐酸羟胺处理，得到3-（2-噻吩基）-4-芳基偶氮基-5-羟基-5-三氟甲基- Δ 2 -isoxazolines 5。随后，5-羟基-5-三氟甲基- Δ的脱水2 -isoxazolines 5到相应的3-（2-噻吩基）-4-芳基偶氮-5- trifluoromethylisoxazoles 6通过用乙酸酐或EtOH-H处理它们来实现2 SO 4。化合物的结构是根据IR，NMR（1 H，13 C和19 F），质谱研究和元素分析。筛选了所有化合物的对四种病原细菌菌株的体外抗菌活性，这些菌株如枯草芽孢杆菌，金黄色葡萄球菌（革兰氏阳性），荧光假单胞菌，大肠杆菌（革兰氏阴性）和对两种病原真菌菌株的体外抗真菌活性。 。念珠菌，酿酒酵母;。大多
• Synthesis, characterization, in vitro DNA photocleavage and cytotoxicity studies of 4-arylazo-1-phenyl-3-(2-thienyl)-5-hydroxy-5-trifluoromethylpyrazolines and regioisomeric 4-arylazo-1-phenyl-5(3)-(2-thienyl)-3(5)-trifluoromethylpyrazoles
  作者：Ranjana Aggarwal、Suresh Kumar、Ashwani Mittal、Rachna Sadana、Vikas Dutt

  DOI：10.1016/j.jfluchem.2020.109573

  日期：2020.8

  1-(2-Thienyl)-2-arylazo-4,4,4-trifluorobutane-1,3-diones (4), generated by the condensation of aryldiazonium salts (2) with 4,4,4-trifluoro-1-(2-thienyl)butane-1,3-dione (3), were used as common intermediates to synthesize regioisomeric 4-arylazo-1-phenyl-5(3)-(2-thienyl)-3(5)-trifluoromethylpyrazoles (5 and 6) and 4-arylazo-1-phenyl-3-(2-thienyl)-5-hydroxy-5-trifluoromethylpyrazolines (7) by reacting

  1-（2-噻吩基）-2-芳基偶氮-4,4,4-三氟丁烷-1,3-二酮（4），是由芳基重氮盐（2）与4,4,4-三氟-1-缩合生成的（2-噻吩基）丁烷-1,3-二酮（3）用作常见的中间体，以合成区域异构的4-芳基偶氮-1-苯基-5（3）-（2-噻吩基）-3（5）-三氟甲基吡唑（5和6）和4-芳基偶氮-1-苯基-3-（2-噻吩基）-5-羟基-5-三氟甲基吡唑啉（7）通过在中性条件下与苯肼反应。所有合成的化合物4，5，6和7在没有任何添加剂的情况下，在λmax 312 nm的紫外线辐射下，筛选pBR322超螺旋DNA质粒的DNA光裂解活性。结果表明3-三氟甲基异构体（5）比相应的5-三氟甲基吡唑（6）和5-羟基5-三氟甲基吡唑啉（7）更好地裂解质粒DNA 。4-（4-硝基苯基偶氮）-1-苯基-5-（2-噻吩基）-3-三氟甲基吡唑5g，显示了作为DNA光切割机的最佳潜力，将超螺旋质粒（Form-I