sodium 2-chloro-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide | 1334394-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: sodium 2-chloro-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide
• 英文别名: sodium 2-chloro-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide
• CAS: 1334394-57-8
• 化学式: C₁₉H₁₄ClF₃N₃O₃S*Na
• 分子量: 479.842
• InChiKey: CYCXWSJGCQTRTH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 sodium 2-chloro-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以90%的产率得到sodium 2-(4-methylpiperazin-1-yl)-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide
  参考文献：
  名称：

  Chemical and in vitro enzymatic stability of newly synthesized celecoxib lipophilic and hydrophilic amides

  摘要：

  Five celecoxib (CXB) acylamide sodium salts, MP-CXB, Cy-CXB, Bz-CXB, CBz-CXB and FBz-CXB were synthesized and characterized. Two simple, fast and validated RP-HPLC methods were developed for simultaneous quantitative determination of the amides and celecoxib in aqueous and biological samples and LOD and LOQ were <= 13.6 and <= 40 ng/mL, respectively. The solubility and logP(app) of the amides, in relevant media, were determined. The chemical hydrolysis, at 60,70 and 80 degrees C, of MP-CXB was studied at GIT-relevant pH (1.2, 6.8 and 7.4) and of CY-CXB was studied at skin relative pH (5.4 and 7.4). Significant hydrolysis was observed for MP-CXB at pH 1.2 only with half-lives 28.28, 11.64 and 3.53h at 60, 70 and 80 degrees C, respectively, with extrapolated half-lives of 2060 and 443 h at 25 and 37 degrees C, respectively. The hydrolysis of all amides was studied in rat live homogenate and only Cy-CXB was hydrolyzed with half-life of 3.79 h. The hydrolysis of MP-CXB and Cy-CXB was studied in human plasma and neither was hydrolyzed. It is finally suggested that hydrophobic interactions plays a role in the binding of susceptible acylamides to the hepatic hydrolyzing enzyme since only amides with saturated hydrocarbon chains underwent hydrolysis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.06.013
• 作为产物：
  描述：

  氯乙酰氯 、 塞来西布 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 24.0h， 以30.2%的产率得到sodium 2-chloro-N-(4-(5-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenylsulfonyl)acetamide
  参考文献：
  名称：

  Chemical and in vitro enzymatic stability of newly synthesized celecoxib lipophilic and hydrophilic amides

  摘要：

  Five celecoxib (CXB) acylamide sodium salts, MP-CXB, Cy-CXB, Bz-CXB, CBz-CXB and FBz-CXB were synthesized and characterized. Two simple, fast and validated RP-HPLC methods were developed for simultaneous quantitative determination of the amides and celecoxib in aqueous and biological samples and LOD and LOQ were <= 13.6 and <= 40 ng/mL, respectively. The solubility and logP(app) of the amides, in relevant media, were determined. The chemical hydrolysis, at 60,70 and 80 degrees C, of MP-CXB was studied at GIT-relevant pH (1.2, 6.8 and 7.4) and of CY-CXB was studied at skin relative pH (5.4 and 7.4). Significant hydrolysis was observed for MP-CXB at pH 1.2 only with half-lives 28.28, 11.64 and 3.53h at 60, 70 and 80 degrees C, respectively, with extrapolated half-lives of 2060 and 443 h at 25 and 37 degrees C, respectively. The hydrolysis of all amides was studied in rat live homogenate and only Cy-CXB was hydrolyzed with half-life of 3.79 h. The hydrolysis of MP-CXB and Cy-CXB was studied in human plasma and neither was hydrolyzed. It is finally suggested that hydrophobic interactions plays a role in the binding of susceptible acylamides to the hepatic hydrolyzing enzyme since only amides with saturated hydrocarbon chains underwent hydrolysis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.06.013