2-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide | 1353056-02-6

• 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-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide
• 英文别名: 2-[5-(4-Fluorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide；2-[5-(4-fluorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide
• CAS: 1353056-02-6
• 化学式: C₁₇H₁₀F₄N₄O₂S₂
• 分子量: 442.418
• InChiKey: DVQWEVASXIISFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  磺胺 在 盐酸 、 hydrazine hydrate 、 溴 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 2-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide 、 2-[3-(4-fluorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl]-1,3-benzothiazole-6-sulfonamide
  参考文献：
  名称：

  Heteroaromatic analogues of 1,5-diarylpyrazole class as anti-inflammatory agents

  摘要：

  A novel series of heteroaromatic analogues of known anti-inflammatory (AI) drug celecoxib replacing the benzenesulfonamide moiety with 6-sulfonamidobenzothiazol-2-yl moiety was synthesized. Regioselective synthesis of the target compounds 2a-i having 1,5-diaryl relationship was achieved by exploring reaction conditions. All the newly synthesized compounds (2a-i and 8) were screened for their in vivo AI activity using carrageenan-induced rat paw edema assay. Five compounds (2c-f and 2i) were found to possess good AI activity (a parts per thousand yen60% inhibition), 3 h after the carrageenan injection when compared to that of standard drug indomethacin (78%), whereas the remaining four compounds (2a-b and 2g-h) with 1,5-diaryl relationship have shown moderate activity with 49-56% inhibition after 3 h. However, pyrazole 8 having 1,3-diaryl relationship failed to show appreciable AI activity.

  DOI：

  10.1007/s00044-011-9898-4

文献信息

• Heteroaromatic analogues of 1,5-diarylpyrazole class as anti-inflammatory agents
  作者：Pawan K. Sharma、Nisha Chandna、Surender Kumar、Pawan Kumar、Satish Kumar、Pawan Kaushik、Dhirender Kaushik

  DOI：10.1007/s00044-011-9898-4

  日期：2012.11

  A novel series of heteroaromatic analogues of known anti-inflammatory (AI) drug celecoxib replacing the benzenesulfonamide moiety with 6-sulfonamidobenzothiazol-2-yl moiety was synthesized. Regioselective synthesis of the target compounds 2a-i having 1,5-diaryl relationship was achieved by exploring reaction conditions. All the newly synthesized compounds (2a-i and 8) were screened for their in vivo AI activity using carrageenan-induced rat paw edema assay. Five compounds (2c-f and 2i) were found to possess good AI activity (a parts per thousand yen60% inhibition), 3 h after the carrageenan injection when compared to that of standard drug indomethacin (78%), whereas the remaining four compounds (2a-b and 2g-h) with 1,5-diaryl relationship have shown moderate activity with 49-56% inhibition after 3 h. However, pyrazole 8 having 1,3-diaryl relationship failed to show appreciable AI activity.