ethyl 1'-(5-(phenylethynyl)furan-2-carbonyl)-2H-spiro[benzofuran-3,4'-piperidine]-5-carbimidate | 1025687-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 1'-(5-(phenylethynyl)furan-2-carbonyl)-2H-spiro[benzofuran-3,4'-piperidine]-5-carbimidate
• CAS: 1025687-95-9
• 化学式: C₂₈H₂₆N₂O₄
• 分子量: 454.525
• InChiKey: YTXRGSIHQUJKMB-UHFFFAOYSA-N

物化性质

• 沸点：
  640.3±65.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 1'-(5-(phenylethynyl)furan-2-carbonyl)-2H-spiro[benzofuran-3,4'-piperidine]-5-carbimidate 在 肼 作用下， 以 乙醇 为溶剂， 以33%的产率得到1-(5-phenylethynyl-furan-2-yl)carbonyl-5'-[hydrazino(imino)methyl]-spiro[piperidine-4,3'-(2H)-benzo[b]furan]
  参考文献：
  名称：

  Potent, nonpeptide inhibitors of human mast cell tryptase. Synthesis and biological evaluation of novel spirocyclic piperidine amide derivatives

  摘要：

  We have explored a series of spirocyclic piperidine amide derivatives ( 5) as tryptase inhibitors. Thus, 4 (JNJ-27390467) was identified as a potent, selective tryptase inhibitor with oral efficacy in two animal models of airway inflammation ( sheep and guinea pig asthma models). An X-ray co-crystal structure of 4 tryptase revealed a hydrophobic pocket in the enzyme's active site, which is induced by the phenylethynyl group and is comprised of amino acid residues from two different monomers of the tetrameric protein. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.093
• 作为产物：
  描述：

  乙醇 、 1'-(5-(phenylethynyl)furan-2-carbonyl)-2H-spiro[benzofuran-3,4'-piperidine]-5-carbonitrile 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以99%的产率得到ethyl 1'-(5-(phenylethynyl)furan-2-carbonyl)-2H-spiro[benzofuran-3,4'-piperidine]-5-carbimidate
  参考文献：
  名称：

  Potent, nonpeptide inhibitors of human mast cell tryptase. Synthesis and biological evaluation of novel spirocyclic piperidine amide derivatives

  摘要：

  We have explored a series of spirocyclic piperidine amide derivatives ( 5) as tryptase inhibitors. Thus, 4 (JNJ-27390467) was identified as a potent, selective tryptase inhibitor with oral efficacy in two animal models of airway inflammation ( sheep and guinea pig asthma models). An X-ray co-crystal structure of 4 tryptase revealed a hydrophobic pocket in the enzyme's active site, which is induced by the phenylethynyl group and is comprised of amino acid residues from two different monomers of the tetrameric protein. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.093