N-methyl-N-(1-methylpiperidin-4-yl)-4-propan-2-ylbenzenesulfonamide | 1135731-33-7

• 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-methyl-N-(1-methylpiperidin-4-yl)-4-propan-2-ylbenzenesulfonamide
• CAS: 1135731-33-7
• 化学式: C₁₆H₂₆N₂O₂S
• 分子量: 310.461
• InChiKey: IQOBETABGVPKIC-UHFFFAOYSA-N

物化性质

• 沸点：
  412.2±55.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 sodium cyanoborohydride 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.25h， 生成 N-methyl-N-(1-methylpiperidin-4-yl)-4-propan-2-ylbenzenesulfonamide
  参考文献：
  名称：

  5-HT2C receptor selectivity and structure–activity relationship of N-methyl-N-(1-methylpiperidin-4-yl)benzenesulfonamide analogs

  摘要：

  Agonists of the 5-HT2C receptor have attracted much attention as therapeutic agents for the treatment of obesity. Subtype selectivity against other 5-HT2 receptors is one of the most important prerequisites for reducing side effects. We present the synthesis of N-methyl-N-(1-methylpiperidin-4-yl) benzenesulfonamide analogs and their structure-activity relationship studies on 5-HT2A and 5-HT2C receptors. Although the compounds showed nanomolar activity to the 5-HT2C receptor, their selectivity against the 5-HT2A receptor was modest to low. Molecular modeling studies using homology modeling and docking simulation revealed that selectivity originated from subtype specific residues. The observed binding modes and receptor-ligand interactions provided us a clue for optimizing the selectivity against the 5-HT2A receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.001

文献信息

• 5-HT2C receptor selectivity and structure–activity relationship of N-methyl-N-(1-methylpiperidin-4-yl)benzenesulfonamide analogs
  作者：Jae Wan Jang、Je-sook Baek、Gil Don Choi、Woo-Kyu Park、Yong Seo Cho、Du-Jong Baek、Ae Nim Pae

  DOI：10.1016/j.bmcl.2011.11.001

  日期：2012.1

  Agonists of the 5-HT2C receptor have attracted much attention as therapeutic agents for the treatment of obesity. Subtype selectivity against other 5-HT2 receptors is one of the most important prerequisites for reducing side effects. We present the synthesis of N-methyl-N-(1-methylpiperidin-4-yl) benzenesulfonamide analogs and their structure-activity relationship studies on 5-HT2A and 5-HT2C receptors. Although the compounds showed nanomolar activity to the 5-HT2C receptor, their selectivity against the 5-HT2A receptor was modest to low. Molecular modeling studies using homology modeling and docking simulation revealed that selectivity originated from subtype specific residues. The observed binding modes and receptor-ligand interactions provided us a clue for optimizing the selectivity against the 5-HT2A receptor. (C) 2011 Elsevier Ltd. All rights reserved.