1-(3,4-Difluorophenyl)-5-(4-methylsulfonylphenyl)imidazole | 1239358-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,4-Difluorophenyl)-5-(4-methylsulfonylphenyl)imidazole
• CAS: 1239358-07-6
• 化学式: C₁₆H₁₂F₂N₂O₂S
• 分子量: 334.346
• InChiKey: UNLBJBHMXDYZGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 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：
  60.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-Difluorophenyl)-5-(4-methylsulfonylphenyl)imidazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以50%的产率得到1-(3,4-difluorophenyl)-4-bromo-5-(4-methylsulfonylphenyl)imidazole
  参考文献：
  名称：

  Synthesis of 1,5-diarylhaloimidazole analogs and their inhibitory activities against PGE2 production from LPS-treated RAW 264.7 cells

  摘要：

  A number of 1,5-diarylimidazole analogs were synthesized and evaluated their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin E-2 production. Reactions of 1,5-diarylimidazoles with halogenating reagents (NCS, NBS, NIS) afforded halogenated analogs. Among the analogs tested, compounds Ib, Ha, IIb and IIe exhibited significantly improved inhibitory activities against COX-2-mediated PGE(2) production from LPS-induced RAW 264.7 cells compared to those of the parent 1,5-diarylimidazoles. Especially, the analogs Ib (IC50 = 0.55 mu M) and Ha (IC50 = 0.58 mu M) showed best results. Halogenation on the 1,5-diarylimidazole ring enhanced inhibitory activities against COX-2 catalyzed PGE(2) production, however, inhibitory activities were significantly varied by position(s) and species of the substituted halogen(s). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.014
• 作为产物：
  描述：

  在 oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 以91%的产率得到1-(3,4-Difluorophenyl)-5-(4-methylsulfonylphenyl)imidazole
  参考文献：
  名称：

  1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells

  摘要：

  A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE(2) production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.092

文献信息

• 1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells
  作者：Haiyan Che、Truong Ngoc Tuyen、Hyun Pyo Kim、Haeil Park

  DOI：10.1016/j.bmcl.2010.05.092

  日期：2010.7

  A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE(2) production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 1,5-diarylhaloimidazole analogs and their inhibitory activities against PGE2 production from LPS-treated RAW 264.7 cells
  作者：Zunhua Yang、Tuyen N. Truong、Tuan-Anh N. Pham、Jae-Won Lee、Sung-Soo Kim、Haeil Park

  DOI：10.1016/j.bmc.2012.09.014

  日期：2012.11

  A number of 1,5-diarylimidazole analogs were synthesized and evaluated their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin E-2 production. Reactions of 1,5-diarylimidazoles with halogenating reagents (NCS, NBS, NIS) afforded halogenated analogs. Among the analogs tested, compounds Ib, Ha, IIb and IIe exhibited significantly improved inhibitory activities against COX-2-mediated PGE(2) production from LPS-induced RAW 264.7 cells compared to those of the parent 1,5-diarylimidazoles. Especially, the analogs Ib (IC50 = 0.55 mu M) and Ha (IC50 = 0.58 mu M) showed best results. Halogenation on the 1,5-diarylimidazole ring enhanced inhibitory activities against COX-2 catalyzed PGE(2) production, however, inhibitory activities were significantly varied by position(s) and species of the substituted halogen(s). (C) 2012 Elsevier Ltd. All rights reserved.