3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-N-(4-fluorophenyl)benzenesulfonamide

• 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: 3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-N-(4-fluorophenyl)benzenesulfonamide
• 英文别名: 3-[(2S,6R)-2,6-dimethylmorpholine-4-carbonyl]-N-(4-fluorophenyl)benzenesulfonamide
• 化学式: C₁₉H₂₁FN₂O₄S
• 分子量: 392.451
• InChiKey: VELZLTKAEUBBBH-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氯磺酰苯甲酰氯 、 cis-2,6-dimethylmorpholine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-N-(4-fluorophenyl)benzenesulfonamide
  参考文献：
  名称：

  Optimization of ADME Properties for Sulfonamides Leading to the Discovery of a T-Type Calcium Channel Blocker, ABT-639

  摘要：

  The discovery of a novel peripherally acting and selective Ca(v)3.2 T-type calcium channel blocker, ABT-639, is described. HTS hits 1 and 2, which have poor metabolic stability, were optimized to obtain 4, which has improved stability and oral bioavailability. Modification of 4 to further improve ADME properties led to the discovery of ABT-639. Following oral administration, ABT-639 produces robust antinociceptive activity in experimental pain models at doses that do not significantly alter psychomotor or hemodynamic function in the rat.

  DOI：

  10.1021/acsmedchemlett.5b00023

文献信息

• Optimization of ADME Properties for Sulfonamides Leading to the Discovery of a T-Type Calcium Channel Blocker, ABT-639
  作者：Qingwei Zhang、Zhiren Xia、Shailen Joshi、Victoria E. Scott、Michael F. Jarvis

  DOI：10.1021/acsmedchemlett.5b00023

  日期：2015.6.11

  The discovery of a novel peripherally acting and selective Ca(v)3.2 T-type calcium channel blocker, ABT-639, is described. HTS hits 1 and 2, which have poor metabolic stability, were optimized to obtain 4, which has improved stability and oral bioavailability. Modification of 4 to further improve ADME properties led to the discovery of ABT-639. Following oral administration, ABT-639 produces robust antinociceptive activity in experimental pain models at doses that do not significantly alter psychomotor or hemodynamic function in the rat.