N-({(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}carbamoyl)benzenesulfonamide | 1189141-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-({(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}carbamoyl)benzenesulfonamide
• 英文别名: 1-(benzenesulfonyl)-3-[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]urea
• CAS: 1189141-97-6
• 化学式: C₂₂H₂₂FN₃O₃S
• 分子量: 427.499
• InChiKey: MCPUMUXGLDOLFP-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-amine dihydrochloride 、 异氰酸苯磺酰酯 在 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.67h， 以30%的产率得到N-({(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}carbamoyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and metabolic stability of acrylamide derivatives as novel CCR3 antagonists

  摘要：

  Our laboratory has identified several acrylamide derivatives with potent CCR3 inhibitory activity. In the present study, we evaluated the in vitro metabolic stability (CL(int); mL/min/kg) of these compounds in human liver microsomes (HLMs), and assessed the relationship between their structures and CLint values. Among the compounds identified, N-{(3R)-1-[(6-fluoro-2-naphthyl) methyl] pyrrolidin-3-yl}-2-[ 1-(2-hydroxybenzoyl) piperidin-4-ylidene] acetamide (30j) was found to be a potent inhibitor (IC(50) = 8.4 nM) with a high metabolic stability against HLMs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.066