tert-butyl 4-(7-(2-((S)-3-((6-chloronaphthalene)-2-sulfonamido)-2-oxopiperidin-1-yl)acetyl)-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)piperidine-1-carboxylate | 1360474-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 4-(7-(2-((S)-3-((6-chloronaphthalene)-2-sulfonamido)-2-oxopiperidin-1-yl)acetyl)-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)piperidine-1-carboxylate
• CAS: 1360474-50-5
• 化学式: C₃₅H₄₆ClN₅O₇S
• 分子量: 716.299
• InChiKey: ZPHLZRRLZXJHMH-YFIBMDDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  49.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  136.64
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(7-(2-((S)-3-((6-chloronaphthalene)-2-sulfonamido)-2-oxopiperidin-1-yl)acetyl)-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 6-chloro-N-[(3S)-2-oxo-1-[2-oxo-2-[7-(piperidine-4-carbonyl)-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethyl]piperidin-3-yl]naphthalene-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
• 作为产物：
  描述：

  tert-butyl 7-(2-((S)-3-((6-chloronaphthalene)-2-sulfonamido)-2-oxopiperidin-1-yl)acetyl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 4-(7-(2-((S)-3-((6-chloronaphthalene)-2-sulfonamido)-2-oxopiperidin-1-yl)acetyl)-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)piperidine-1-carboxylate
  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