4-bromo-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]benzenesulfonamide | 1350909-17-9

• 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-bromo-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]benzenesulfonamide
• CAS: 1350909-17-9
• 化学式: C₁₇H₂₂BrN₃O₄S
• 分子量: 444.349
• InChiKey: BJLQOMYICWNUJR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-[[(3S)-3-amino-2-oxo-1-piperidinyl]acetyl]pyrrolidine 、 4-溴苯磺酰氯 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 生成 4-bromo-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Arylsulfonamidopiperidone derivatives as a novel class of factor Xa inhibitors

  摘要：

  The design, synthesis and SAR of a novel class of valerolactam-based arylsulfonamides as potent and selective FXa inhibitors is reported. The arylsulfonamide-valerolactam scaffold was derived based on the proposed bioisosterism to the arylcyanoguanidine-caprolactam core in known FXa inhibitors. The SAR study led to compound 46 as the most potent FXa inhibitor in this series, with an IC50 of 7 nM and EC2xPT of 1.7 mu M. The X-ray structure of compound 40 bound to FXa shows that the sulfonamide-valerolactam scaffold anchors the aryl group in the S1 and the novel acylcytisine pharmacophore in the S4 pockets. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.098