N-((S)-1-((1S,2R,4R)-4-amino-2-((tert-butylsulfonyl)methyl)cyclohexyl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide | 1610775-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-((S)-1-((1S,2R,4R)-4-amino-2-((tert-butylsulfonyl)methyl)cyclohexyl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide
• CAS: 1610775-99-9
• 化学式: C₂₃H₃₂F₃N₃O₄S
• 分子量: 503.586
• InChiKey: FYQQWDPDRSWEEK-NQYYFHDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-((S)-1-((1S,2R,4R)-4-amino-2-((tert-butylsulfonyl)methyl)cyclohexyl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(3S)-1-[(1S,2R,4R)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Alkylsulfone-containing trisubstituted cyclohexanes as potent and bioavailable chemokine receptor 2 (CCR2) antagonists

  摘要：

  We describe novel alkylsulfones as potent CCR2 antagonists with reduced hERG channel activity and improved pharmacokinetics over our previously described antagonists. Several of these new alkylsulfones have a profile that includes functional antagonism of CCR2, in vitro microsomal stability, and oral bioavailability. With this improved profile, we demonstrate that two of these antagonists, 2 and 12, are orally efficacious in an animal model of inflammatory recruitment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.013
• 作为产物：
  描述：

  tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate 在 N-甲基吗啉 、 palladium on activated charcoal 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 caesium carbonate 、 臭氧 、 三氟乙酸 、 碘甲烷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 N-((S)-1-((1S,2R,4R)-4-amino-2-((tert-butylsulfonyl)methyl)cyclohexyl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Alkylsulfone-containing trisubstituted cyclohexanes as potent and bioavailable chemokine receptor 2 (CCR2) antagonists

  摘要：

  We describe novel alkylsulfones as potent CCR2 antagonists with reduced hERG channel activity and improved pharmacokinetics over our previously described antagonists. Several of these new alkylsulfones have a profile that includes functional antagonism of CCR2, in vitro microsomal stability, and oral bioavailability. With this improved profile, we demonstrate that two of these antagonists, 2 and 12, are orally efficacious in an animal model of inflammatory recruitment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.013