2-{4-[4-chloro-1-(4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl]-2-fluorophenoxy}ethanol | 935532-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{4-[4-chloro-1-(4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl]-2-fluorophenoxy}ethanol
• 英文别名: 2-[4-[5-chloro-3-(4-methylsulfonylphenyl)imidazol-4-yl]-2-fluorophenoxy]ethanol
• CAS: 935532-47-1
• 化学式: C₁₈H₁₆ClFN₂O₄S
• 分子量: 410.853
• InChiKey: PHYFTWIBLMEKAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{4-[4-chloro-1-(4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl]-2-fluorophenoxy}ethanol 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以35%的产率得到2-{4-[4-chloro-1-(4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl]-2-fluorophenoxy}ethyl Nitrate
  参考文献：
  名称：

  NO-Donor COX-2 Inhibitors. New Nitrooxy-Substituted 1,5-Diarylimidazoles Endowed with COX-2 Inhibitory and Vasodilator Properties

  摘要：

  A series of NO-donor diarylimidazoles derived from the lead compound Cimicoxib were synthesized and evaluated for their COX-2 inhibitory activity and their stability in whole blood as well as for vasodilator properties. The products are partly transformed into the corresponding alcohols following 24-h incubation in whole blood. All of them display good COX-1/COX-2 selectivity, but are less potent than the lead; a molecular modeling study was carried out to investigate their binding mode. The compounds are also capable of relaxing rat aorta strips precontracted with phenylephrine with a NO-dependent mechanism; this property could confer reduced cardiotoxicity with respect to traditional COX-2 inhibitors.

  DOI：

  10.1021/jm0607247
• 作为产物：
  描述：

  4-chloro-5-(3-fluoro-4-hydroxyphenyl)-1-(4-methylsulfonylphenyl)imidazole 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-{4-[4-chloro-1-(4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl]-2-fluorophenoxy}ethanol
  参考文献：
  名称：

  NO-Donor COX-2 Inhibitors. New Nitrooxy-Substituted 1,5-Diarylimidazoles Endowed with COX-2 Inhibitory and Vasodilator Properties

  摘要：

  A series of NO-donor diarylimidazoles derived from the lead compound Cimicoxib were synthesized and evaluated for their COX-2 inhibitory activity and their stability in whole blood as well as for vasodilator properties. The products are partly transformed into the corresponding alcohols following 24-h incubation in whole blood. All of them display good COX-1/COX-2 selectivity, but are less potent than the lead; a molecular modeling study was carried out to investigate their binding mode. The compounds are also capable of relaxing rat aorta strips precontracted with phenylephrine with a NO-dependent mechanism; this property could confer reduced cardiotoxicity with respect to traditional COX-2 inhibitors.

  DOI：

  10.1021/jm0607247