tert-butyl 4-[2-[[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]amino]-2-oxoethylidene]piperidine-1-carboxylate | 671207-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 4-[2-[[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]amino]-2-oxoethylidene]piperidine-1-carboxylate
• CAS: 671207-13-9
• 化学式: C₂₇H₃₄FN₃O₃
• 分子量: 467.584
• InChiKey: ZRMUVNGZGFVCOJ-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[2-[[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]amino]-2-oxoethylidene]piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到N-((3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl)-2-piperidin-4-ylideneacetamide
  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
• 作为产物：
  描述：

  diethyl[2-({(3E)-1-[(6-fluoro-2-naphthyl)methyl]-pyrrolidin-3-yl}amino)-2-oxoethyl]phosphonate 、 N-叔丁氧羰基-4-哌啶酮 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 反应 3.5h， 以100%的产率得到tert-butyl 4-[2-[[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]amino]-2-oxoethylidene]piperidine-1-carboxylate
  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