4-chloro-N-[2-(4-{1,1-dimethyl-2-oxo-2[(phenylsulfonyl)amino]ethoxy}phenyl)ethyl]benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-[2-(4-{1,1-dimethyl-2-oxo-2[(phenylsulfonyl)amino]ethoxy}phenyl)ethyl]benzamide
• 英文别名: N-[2-[4-[1-(benzenesulfonamido)-2-methyl-1-oxopropan-2-yl]oxyphenyl]ethyl]-4-chlorobenzamide
• 化学式: C₂₅H₂₅ClN₂O₅S
• 分子量: 501.003
• InChiKey: ROQBYXMBUNMDFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯磺酰胺 、 苯扎贝特 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以60%的产率得到4-chloro-N-[2-(4-{1,1-dimethyl-2-oxo-2[(phenylsulfonyl)amino]ethoxy}phenyl)ethyl]benzamide
  参考文献：
  名称：

  Synthesis, in vitro evaluation, and molecular modeling investigation of benzenesulfonimide peroxisome proliferator-activated receptors α antagonists

  摘要：

  Recent evidences suggest a moderate activation of Peroxisome Proliferator-Activated Receptors (PPARs) could be favorable in metabolic diseases, reducing side effects given from full agonists. PPAR partial agonists and antagonists represent, to date, interesting tools to better elucidate biological processes modulated by these receptors. In this work are reported new benzenesulfonimide compounds able to block PPAR alpha, synthesized and tested by transactivation assays and gene expression analysis. Some of these compounds showed a dose-dependent antagonistic behavior on PPAR alpha, submicromolar potency, different profiles of selectivity versus PPAR gamma, and a repressive effect on CPT1A expression. Dockings and molecular dynamics on properly selected benzenesulfonimide derivatives furnished fresh insights into the molecular determinant most likely responsible for PPARa antagonism. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.064

文献信息

• Synthesis, in vitro evaluation, and molecular modeling investigation of benzenesulfonimide peroxisome proliferator-activated receptors α antagonists
  作者：Alessandra Ammazzalorso、Antonio Carrieri、Fabio Verginelli、Isabella Bruno、Giuseppe Carbonara、Alessandra D'Angelo、Barbara De Filippis、Marialuigia Fantacuzzi、Rosalba Florio、Giuseppe Fracchiolla、Letizia Giampietro、Antonella Giancristofaro、Cristina Maccallini、Alessandro Cama、Rosa Amoroso

  DOI：10.1016/j.ejmech.2016.02.064

  日期：2016.5

  Recent evidences suggest a moderate activation of Peroxisome Proliferator-Activated Receptors (PPARs) could be favorable in metabolic diseases, reducing side effects given from full agonists. PPAR partial agonists and antagonists represent, to date, interesting tools to better elucidate biological processes modulated by these receptors. In this work are reported new benzenesulfonimide compounds able to block PPAR alpha, synthesized and tested by transactivation assays and gene expression analysis. Some of these compounds showed a dose-dependent antagonistic behavior on PPAR alpha, submicromolar potency, different profiles of selectivity versus PPAR gamma, and a repressive effect on CPT1A expression. Dockings and molecular dynamics on properly selected benzenesulfonimide derivatives furnished fresh insights into the molecular determinant most likely responsible for PPARa antagonism. (C) 2016 Elsevier Masson SAS. All rights reserved.