2'-benzoxazol-2-yl-3-chlorobiphenyl-4-ol | 1239313-13-3

• 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'-benzoxazol-2-yl-3-chlorobiphenyl-4-ol
• 英文别名: 4-[2-(1,3-Benzoxazol-2-yl)phenyl]-2-chlorophenol；4-[2-(1,3-benzoxazol-2-yl)phenyl]-2-chlorophenol
• CAS: 1239313-13-3
• 化学式: C₁₉H₁₂ClNO₂
• 分子量: 321.763
• InChiKey: UEBSFCVHMRZVIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-溴苯基)-1,3-苯并恶唑 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 30.0~165.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 生成 2'-benzoxazol-2-yl-3-chlorobiphenyl-4-ol
  参考文献：
  名称：

  2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation

  摘要：

  The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2). The 2-(2-arylphenyl)benzoxazoles 3a-m have been synthesized by Suzuki reaction of 2-(2-bromophenyl)benzoxazole. Further synthetic manipulation of 3f and 3i led to 3o and 3n, respectively. The compounds 3g, 3n, and 3o selectively inhibited COX-2 with selectivity index of 3n much better than that of the COX-2 selective NSAID celecoxib. The in vivo anti-inflammatory potency of 3g and 3n is comparable to that of celecoxib and the nonselective NSAID diclofenac at two different doses, and 30 showed better potency compared to these clinically used NSAIDs.

  DOI：

  10.1021/ml400500e

文献信息

• 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation
  作者：Kapileswar Seth、Sanjeev K. Garg、Raj Kumar、Priyank Purohit、Vachan S. Meena、Rohit Goyal、Uttam C. Banerjee、Asit K. Chakraborti

  DOI：10.1021/ml400500e

  日期：2014.5.8

  The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2). The 2-(2-arylphenyl)benzoxazoles 3a-m have been synthesized by Suzuki reaction of 2-(2-bromophenyl)benzoxazole. Further synthetic manipulation of 3f and 3i led to 3o and 3n, respectively. The compounds 3g, 3n, and 3o selectively inhibited COX-2 with selectivity index of 3n much better than that of the COX-2 selective NSAID celecoxib. The in vivo anti-inflammatory potency of 3g and 3n is comparable to that of celecoxib and the nonselective NSAID diclofenac at two different doses, and 30 showed better potency compared to these clinically used NSAIDs.