methyl 5-(4-fluorophenyl)-1-(4-methanesulfonylphenyl)-1H-pyrazole-3-carboxylate | 1046152-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-(4-fluorophenyl)-1-(4-methanesulfonylphenyl)-1H-pyrazole-3-carboxylate
• 英文别名: methyl 5-(4-fluorophenyl)-1-(2-nitrophenyl)-1H-pyrazole-3-carboxylate
• CAS: 1046152-05-9
• 化学式: C₁₈H₁₅FN₂O₄S
• 分子量: 374.393
• InChiKey: CILHXYGOOSLFIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.26
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-fluorophenyl)-1-(4-methanesulfonylphenyl)-1H-pyrazole-3-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以63%的产率得到5-(4-Fluorophenyl)-1-(4-methylsulfonylphenyl)pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids: Synthesis, nitric oxide release studies and anti-inflammatory activities

  摘要：

  A new group of hybrid nitric oxide-releasing anti-inflammatory drugs (NONO-coxibs) wherein an O(2)-acetoxymethyl-1-(N-ethyl-N-methylamino)diazen-1-ium-1,2-diolate (11a-c) NO-donor moiety is attached directly to the carboxylic acid group of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids were synthesized. The diazen-1-ium-1,2-diolate compounds 11a-c all released a low amount of NO upon incubation with phosphate buffer (PBS) at pH 7.4 (7.7-9.3% range). In comparison, the percentage of NO released was significantly higher (67.5-73.6% of the theoretical maximal release of two molecules of NO/molecule of the parent hybrid ester prodrug) when the diazen-1-ium-1,2-diolate ester prodrugs were incubated in the presence of rat serum. These incubation studies suggest that both NO and the anti-inflammatory 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3- carboxylic acid (9a-c) would be released from the parent NONO-coxib upon in vivo cleavage by non-specific serum esterases. The 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3- carboxylic acids (9a-c) exhibited AI activities (ID(50) = 85.2-104.4 mg/kg po range) between that exhibited by the reference drugs aspirin (ID(50) = 128.7 mg/kg po) and celecoxib (ID(50) = 10.8 mg/kg po). Hybrid ester anti-inflammatory/NO-donor prodrugs (NONO-coxibs) offers a potential drug design concept targeted toward the development of anti-inflammatory drugs that are devoid of adverse ulcerogenic and/or cardiovascular effects. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.028
• 作为产物：
  描述：

  4-氟苯乙酮 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 5-(4-fluorophenyl)-1-(4-methanesulfonylphenyl)-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Development of 1,5-Diaryl-Pyrazole-3-Formate Analogs as Antifungal Pesticides and Their Application in Controlling Peanut Stem Rot Disease

  摘要：

  3-氯吡啶基团赋予化合物6与甲基异硫氰酸甲酯和噻嗪酰胺对硬皮病菌的抗真菌作用相当，且呈剂量依赖性。

  DOI：

  10.3389/fmicb.2021.728173