3-(2-aminophenyl)-N-[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylpropanamide | 1233497-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-aminophenyl)-N-[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylpropanamide
• CAS: 1233497-39-6
• 化学式: C₂₆H₂₃F₃N₄O₃S
• 分子量: 528.555
• InChiKey: OYVVFSVBGBKCOH-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(2-aminophenyl)-N-[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylpropanamide 生成 塞来西布
  参考文献：
  名称：

  [EN] TARGETING PRODRUGS AND COMPOSITIONS FOR THE TREATMENT OF GASTROINTESTINAL DISEASES
  [FR] PROMÉDICAMENTS CIBLANTS ET COMPOSITIONS DESTINÉS AU TRAITEMENT DE MALADIES GASTRO-INTESTINALES

  摘要：

  公开号：

  WO2010072734A3
• 作为产物：
  描述：

  (2-{3-oxo-3-[4-(5-p-tolyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonylamino]-propyl}-phenyl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-aminophenyl)-N-[4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylpropanamide
  参考文献：
  名称：

  A double prodrug system for colon targeting of benzenesulfonamide COX-2 inhibitors

  摘要：

  The design, synthesis and delivery potential of a new type of benzenesulfonamide cyclo-oxygenase-2 (COX-2) inhibitor prodrug is investigated using celecoxib. The approach involves a double prodrug that is activated first by azoreductases and then by cyclization triggering drug release.We studied the intramolecular aminolysis of the acylsulfonamide. The cyclization was surprisingly rapid at physiological pH and very fast at pH 5. The prodrug is activated specifically under conditions found in the colon but highly stable in the presence of human and rodent intestinal extracts. Finally, the prototype with celecoxib was transported much more slowly in the Caco-2 transepithelial model than the parent. The design therefore shows significant promise for the site specific delivery of benzenesulfonamide COX-2 inhibitors to the colon. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.071

文献信息

• TARGETING PRODRUGS AND COMPOSITIONS FOR THE TREATMENT OF GASTROINTESTINAL DISEASES
  申请人：Gilmer John Francis

  公开号：US20120094963A1

  公开（公告）日：2012-04-19

  Provided herein are compounds of formula (I) as well as compounds of formula (I) which are prodrugs in which the (R7)a-phenyl-S(O)2NH group represents a sulphonamide-bond compound, compositions and methods for preventing or treating gastrointestinal diseases such as inflammatory bowel disease and colorectal cancer, wherein the method comprises delivering an effective amount of a COX-2 or a similar sulphonamide inhibitor as a prodrug or a derivative thereof to the colon, wherein the COX-2 or similar inhibitor is released in vivo.