2-[1-(2-fluorophenyl)-1H-[1,2,3]triazol-4-ylmethylsulfanyl]benzoxazole | 1614257-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[1-(2-fluorophenyl)-1H-[1,2,3]triazol-4-ylmethylsulfanyl]benzoxazole
• 英文别名: 2-[[1-(2-Fluorophenyl)triazol-4-yl]methylsulfanyl]-1,3-benzoxazole；2-[[1-(2-fluorophenyl)triazol-4-yl]methylsulfanyl]-1,3-benzoxazole
• CAS: 1614257-23-6
• 化学式: C₁₆H₁₁FN₄OS
• 分子量: 326.354
• InChiKey: YOUTVOXKKLOMJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-巯基苯并恶唑 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 0.58h， 生成 2-[1-(2-fluorophenyl)-1H-[1,2,3]triazol-4-ylmethylsulfanyl]benzoxazole
  参考文献：
  名称：

  Synthesis of novel 2-mercaptobenzoxazole based 1,2,3-triazoles as inhibitors of proinflammatory cytokines and suppressors of COX-2 gene expression

  摘要：

  A library of novel bis-heterocycles containing 2-mercaptobenzoxazole based 1,2,3-triazoles has been synthesized using click chemistry approach. The compound 4 exhibited the most potent in vivo anti-inflammatory activity with 66.66% and 61.11% inhibition in comparison to celecoxib which showed 72.22% and 65.55% inhibition after 3 h and 5 h respectively. The compounds 4 and 9 suppressed the COX-2 gene expression by 0.94 and 0.79 fold and exhibited a selective index (COX-1/COX-2) of 64.79 and 66.47 respectively in comparison to celecoxib (SI value of 75.56). The in silico molecular docking studies showed the interactions of these molecules with Tyr-59, Tyr-119 and Gly-121. When compared with the standard drug celecoxib, compounds 4, 5, 7, 9 and 16 did not cause any gastric ulceration. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.012