4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-imidazole-2(3H)-thione | 464153-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-imidazole-2(3H)-thione
• 英文别名: 4-(4-Chlorophenyl)-5-(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione
• CAS: 464153-68-2
• 化学式: C₁₆H₁₃ClN₂OS
• 分子量: 316.811
• InChiKey: BQEHYOYOQFMHIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-imidazole-2(3H)-thione 在 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 5-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-methyl-2-(methylthio)-1H-imidazole
  参考文献：
  名称：

  Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1H-imidazole

  摘要：

  A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717670
• 作为产物：
  描述：

  2-bromo-2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanone 在 sodium methylate 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 1.0h， 生成 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-1H-imidazole-2(3H)-thione
  参考文献：
  名称：

  Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1H-imidazole

  摘要：

  A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717670

文献信息

• 2-Mercapto-4,5-diarylimidazole derivatives and the use thereof as cyclooxygenase inhibitors
  申请人：——

  公开号：US20040116695A1

  公开（公告）日：2004-06-17

  The invention relates to the 2-mercapto-4,5-diarylimidazole derivatives of formula (I), wherein R 1 , R 2 , R 3 and R 4 are defined as in the description. The inventive compounds have an immunomodulatory and cyclooxygenase-inhibiting activity and are therefore suitable for the treatment of diseases that are associated with a disturbed immune system.

  本发明涉及公式(I)的2-巯基-4,5-二芳基咪唑衍生物，其中R1、R2、R3和R4如描述中所定义。该发明化合物具有免疫调节和环氧合酶抑制活性，因此适用于治疗与免疫系统紊乱有关的疾病。
• 2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors
  申请人：Dannhardt Gerd

  公开号：US20070185169A1

  公开（公告）日：2007-08-09

  The invention relates to the 2-mercapto-4,5-diarylimidazole derivatives of formula (I), wherein R 1 , R 2 , R 3 and R 4 are defined as in the description. The inventive compounds have an immunomodulatory and cyclooxygenase-inhibiting activity and are therefore suitable for the treatment of disease that are associated with a disturbed immune system.

  本发明涉及公式（I）中的2-巯基-4,5-二芳基咪唑衍生物，其中R1、R2、R3和R4如说明书中所定义。这些创新化合物具有免疫调节和环氧合酶抑制活性，因此适用于治疗与免疫系统紊乱相关的疾病。
• Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors
  作者：Amir Assadieskandar、Mohsen Amini、Marjan Salehi、Hamid Sadeghian、Maliheh Alimardani、Amirhossein Sakhteman、Hamid Nadri、Abbas Shafiee

  DOI：10.1016/j.bmc.2012.09.050

  日期：2012.12

  A series of 4,5-diaryl-1H-imidazole-2(3H)-thione was synthesized and their inhibitory potency against soybean 15-lipoxygenase and free radical scavenging activities were determined. Compound 11 showed the best IC50 for 15-LOX inhibition (IC50 = 4.7 mu M) and free radical scavenging activity (IC50 = 14 mu M). Methylation of SH at C-2 position of imidazole has dramatically decreased the 15-LOX inhibition and radical scavenging activity as it can be observed in the inactive compound 14 (IC50 >250 mu M). Structure activity similarity (SAS) showed that the most important chemical modification in this series was methylation of SH group and Docking studies revealed a proper orientation for SH group towards Fe core of the 15-LOX active site. Therefore it was concluded that iron chelating could be a possible mechanism for enzyme inhibition in this series of compounds. (C) 2012 Elsevier Ltd. All rights reserved.
• US7223781B2
  申请人：——

  公开号：US7223781B2

  公开（公告）日：2007-05-29
• Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1<i>H</i>-imidazole
  作者：Amir Assadieskandar、Marjan Salehi、Mohsen Vosooghi、Abbas Shafiee、Mohsen Amini

  DOI：10.1080/00397911.2012.717670

  日期：2013.9.17

  A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.