4-chloro-N-methyl-N-(1-methyl-piperidin-4-yl)-benzenesulfonamide | 797807-30-8

• 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-methyl-N-(1-methyl-piperidin-4-yl)-benzenesulfonamide
• 英文别名: 4-chloro-N-methyl-N-(1-methylpiperidin-4-yl)benzenesulfonamide
• CAS: 797807-30-8
• 化学式: C₁₃H₁₉ClN₂O₂S
• 分子量: 302.825
• InChiKey: WGYOBGCPSCGBPS-UHFFFAOYSA-N

物化性质

• 沸点：
  407.2±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  >45.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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 4-chloro-N-methyl-N-(1-methyl-piperidin-4-yl)-benzenesulfonamide
  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

• N-substituted benzene sulfonamides
  申请人：Elan Pharmaceuticals Inc.

  公开号：EP2360142A1

  公开（公告）日：2011-08-24

  The invention provides N-substituted benzenesulfonamides for use in treating or preventing cognitive disorders, such as Alzheimer's Disease. Compounds of particular interest are defined by Formula (I), wherein R1, R2, R3, R4, and R3, are as described in the specification. The invention also encompasses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of treating cognitive disorders, including Alzheimer's disease using compounds of Formula (I).

  本发明提供了用于治疗或预防认知障碍（如阿尔茨海默病）的 N-取代苯磺酰胺类化合物。特别感兴趣的化合物由式（I）定义，其中 R1、R2、R3、R4 和 R3 如说明书所述。本发明还包括由式（I）化合物组成的药物组合物以及使用式（I）化合物治疗认知障碍（包括阿尔茨海默病）的方法。
• N-SUBSTITUTED BENZENE SULFONAMIDES
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1723102A2

  公开（公告）日：2006-11-22
• US8193389B2
  申请人：——

  公开号：US8193389B2

  公开（公告）日：2012-06-05
• [EN] N-SUBSTITUTED BENZENE SULFONAMIDES<br/>[FR] BENZENE SULFONAMIDES N-SUBSTITUES
  申请人：ELAN PHARM INC

  公开号：WO2005090296A2

  公开（公告）日：2005-09-29

  The invention provides N-substituted benzenesulfonamides for use in treating or preventing cognitive disorders, such as Alzheimer's Disease. Compounds of particular interest are defined by Formula (I), wherein R1, R2, R3, R4, and R3, are as described in the specification. The invention also encompasses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of treating cognitive disorders, including Alzheimer's disease using compounds of Formula (I).
• 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.