N-(4-bromophenyl)-N-butylbenzenesulfonamide

• 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: N-(4-bromophenyl)-N-butylbenzenesulfonamide
• 英文别名: N-(4-bromophenyl)-N-butylbenzenesulfonamide
• 化学式: C₁₆H₁₈BrNO₂S
• 分子量: 368.294
• InChiKey: KDPUMSWDSZFFQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

   N-(4-bromophenyl)-N-butylbenzenesulfonamide 在 2-甲胺乙硫醇盐酸盐 、 溶剂黄146 、 N,N-二异丙基乙胺 、 palladium dichloride 作用下， 以 N-甲基吡咯烷酮 、 乙腈 为溶剂， 反应 6.0h， 生成 N-butyl-N-(4-(hydroxydimethylsilyl)phenyl)benzenesulfonamide
  参考文献：
  名称：

  Development of novel silanol-based human pregnane X receptor (PXR) agonists with improved receptor selectivity

  摘要：

  Pregnane X receptor (PXR) is a ligand-dependent transcription factor that is considered to be a potential therapeutic target for multiple diseases. Herein, we report the development and structure-activity relationship studies of a new series of hPXR agonists. Focusing on our recently developed silanol-sulfonamide scaffold, we developed the potent hPXR agonist 28, which shows good selectivity over hLXR alpha and beta, hFXR, and hROR alpha and gamma. Examination of the structure-activity relationship suggested a possible strategy to manipulate the selectivity. Docking simulation indicated the presence of an additional binding cavity and polar contacts in the ligand-binding pocket of hPXR. This information should be helpful for the future development of more potent and selective hPXR ligands.

  DOI：

  10.1016/j.bmc.2018.07.038
• 作为产物：
  描述：

  4-溴苯胺 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成  N-(4-bromophenyl)-N-butylbenzenesulfonamide
  参考文献：
  名称：

  Development of novel silanol-based human pregnane X receptor (PXR) agonists with improved receptor selectivity

  摘要：

  Pregnane X receptor (PXR) is a ligand-dependent transcription factor that is considered to be a potential therapeutic target for multiple diseases. Herein, we report the development and structure-activity relationship studies of a new series of hPXR agonists. Focusing on our recently developed silanol-sulfonamide scaffold, we developed the potent hPXR agonist 28, which shows good selectivity over hLXR alpha and beta, hFXR, and hROR alpha and gamma. Examination of the structure-activity relationship suggested a possible strategy to manipulate the selectivity. Docking simulation indicated the presence of an additional binding cavity and polar contacts in the ligand-binding pocket of hPXR. This information should be helpful for the future development of more potent and selective hPXR ligands.

  DOI：

  10.1016/j.bmc.2018.07.038

文献信息

• Development of novel silanol-based human pregnane X receptor (PXR) agonists with improved receptor selectivity
  作者：Hirozumi Toyama、Hitoshi Shirakawa、Michio Komai、Yuichi Hashimoto、Shinya Fujii

  DOI：10.1016/j.bmc.2018.07.038

  日期：2018.8

  Pregnane X receptor (PXR) is a ligand-dependent transcription factor that is considered to be a potential therapeutic target for multiple diseases. Herein, we report the development and structure-activity relationship studies of a new series of hPXR agonists. Focusing on our recently developed silanol-sulfonamide scaffold, we developed the potent hPXR agonist 28, which shows good selectivity over hLXR alpha and beta, hFXR, and hROR alpha and gamma. Examination of the structure-activity relationship suggested a possible strategy to manipulate the selectivity. Docking simulation indicated the presence of an additional binding cavity and polar contacts in the ligand-binding pocket of hPXR. This information should be helpful for the future development of more potent and selective hPXR ligands.