4-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide | 678987-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide
• 英文别名: 4-[5-(4-bromophenyl)-3-(trifluoromethyl)pyrazol-1-yl]-2-(hydroxymethyl)benzenesulfonamide
• CAS: 678987-59-2
• 化学式: C₁₇H₁₃BrF₃N₃O₃S
• 分子量: 476.274
• InChiKey: NSHHMWCQJXIHES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide 在 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-[5-(4-bromophenyl)-3-trifluoromethylpyrazol-1-yl]-2-hydroxymethyl-N-propionylbenzenesulfonamide sodium salt
  参考文献：
  名称：

  N-Acylated sulfonamide sodium salt: A prodrug of choice for the bifunctional 2-hydroxymethyl-4-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl) benzenesulfonamide class of COX-2 inhibitors

  摘要：

  Synthesis and biological evaluation of possible prodrugs of COX-2 inhibitors involving sulfonamide and hydroxymethyl groups of 2-hydroxymethyl-4-(5-phenyl-3-trifluoromethyl-pyrazol-1-yl) benzenesulfonamides are described. Out of many options, the sodium salt of N-propionyl sulfonamide demonstrated much improved pharmacological profiles and physicochemical properties suitable for oral as well as parenteral administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.028
• 作为产物：
  描述：

  1-(4-溴苯基)-4,4,4-三氟-1,3-丁二酮 、 4-hydrazino-2-hydroxymethyl-1-benzenesulfonamide hydrochloride 以 乙醇 为溶剂， 反应 11.0h， 生成 4-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-2-hydroxymethyl-benzenesulfonamide
  参考文献：
  名称：

  Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

  摘要：

  Several chemical modifications in the N-1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.027