6-chloro-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]-1H-benzimidazole-2-sulfonamide | 445270-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-chloro-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]-1H-benzimidazole-2-sulfonamide
• CAS: 445270-99-5
• 化学式: C₁₈H₂₂ClN₅O₄S
• 分子量: 439.923
• InChiKey: WUESRISJSXUOKK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[[(3S)-3-amino-2-oxo-1-piperidinyl]acetyl]pyrrolidine 、 6-Chloro-1H-benzimidazole-2-sulfonyl chloride 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 生成 6-chloro-N-[(3S)-2-oxo-1-(2-oxo-2-pyrrolidin-1-ylethyl)piperidin-3-yl]-1H-benzimidazole-2-sulfonamide
  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

文献信息

• Arylsulfonamidopiperidone derivatives as a novel class of factor Xa inhibitors
  作者：Yan Shi、Stephen P. O’Connor、Doree Sitkoff、Jing Zhang、Mengxiao Shi、Sharon N. Bisaha、Ying Wang、Chi Li、Zheming Ruan、R. Michael Lawrence、Herbert E. Klei、Kevin Kish、Eddie C.-K. Liu、Steve M. Seiler、Liang Schweizer、Thomas E. Steinbacher、William A. Schumacher、Jeffrey A. Robl、John E. Macor、Karnail S. Atwal、Philip D. Stein

  DOI：10.1016/j.bmcl.2011.06.098

  日期：2011.12

  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.