1-苯乙基-1,3,8-三氮杂-螺[4.5]癸烷-4-酮 | 1026651-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 1-苯乙基-1,3,8-三氮杂-螺[4.5]癸烷-4-酮
• 英文名称: 1-(2-Phenylethyl)-1,3,8-triazaspiro[4.5]decan-4-one
• CAS: 1026651-90-0
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: HNYQKKSXVKHDII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苯乙基-1,3,8-三氮杂-螺[4.5]癸烷-4-酮 在 sodium hydride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 23.5h， 生成 Tert-butyl 3-(2-methoxy-2-oxoethyl)-4-oxo-1-(2-phenylethyl)-1,3,8-triazaspiro[4.5]decane-8-carboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Pseudopeptide Bradykinin B2 Receptor Antagonists Containing the 1,3,8-Triazaspiro[4.5]decan-4-one Ring System

  摘要：

  A series of pseudopeptides containing alkyl-, cycloalkyl-, aryl-, and aralkyl-substituted 1,3,8-triazaspiro[4.5]decan-4-one-3-acetic acids as amino acid surrogates to replace the Pro(2)-Pro(3)-Gly(4)-Phe(5) section of the peptide bradykinin B2 receptor antagonist [Pro(3), Phe(5)]HOE 140 (D-Arg(0)-Arg(1)-Pro(2)-Pro(3)-Gly(4)-Phe(5)-Ser(6)-D-Tic(7)-Oic(8)-Arg(9)) were prepared. These psuedopeptides were examined in vitro for their B2 receptor affinities as well as for their ability to block bradykinin mediated actions in, vivo. Two compounds in particular, NPC 18521 (I) and NPC 18688 (V) were quite potent in these latter assays, indicating that a significant portion of this prototypical second generation decapeptide antagonist can be replaced with a more compact nonpeptide molecule.

  DOI：

  10.1021/jm950676i
• 作为产物：
  描述：

  1-Benzyl-4-(phenethylamino)piperidine-4-carbonitrile 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 136.0h， 生成 1-苯乙基-1,3,8-三氮杂-螺[4.5]癸烷-4-酮
  参考文献：
  名称：

  Synthesis and Characterization of Pseudopeptide Bradykinin B2 Receptor Antagonists Containing the 1,3,8-Triazaspiro[4.5]decan-4-one Ring System

  摘要：

  A series of pseudopeptides containing alkyl-, cycloalkyl-, aryl-, and aralkyl-substituted 1,3,8-triazaspiro[4.5]decan-4-one-3-acetic acids as amino acid surrogates to replace the Pro(2)-Pro(3)-Gly(4)-Phe(5) section of the peptide bradykinin B2 receptor antagonist [Pro(3), Phe(5)]HOE 140 (D-Arg(0)-Arg(1)-Pro(2)-Pro(3)-Gly(4)-Phe(5)-Ser(6)-D-Tic(7)-Oic(8)-Arg(9)) were prepared. These psuedopeptides were examined in vitro for their B2 receptor affinities as well as for their ability to block bradykinin mediated actions in, vivo. Two compounds in particular, NPC 18521 (I) and NPC 18688 (V) were quite potent in these latter assays, indicating that a significant portion of this prototypical second generation decapeptide antagonist can be replaced with a more compact nonpeptide molecule.

  DOI：

  10.1021/jm950676i

文献信息

• HETEROCYCLIC COMPOUNDS AS CCR5 ANTAGONISTS
  申请人：AQUINO Christopher Joseph

  公开号：US20090053172A1

  公开（公告）日：2009-02-26

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable derivatives thereof, useful in the treatment of CCR5-related diseases and disorders, for example, useful in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及式(I)化合物或其药学上可接受的衍生物，用于治疗CCR5相关的疾病和障碍，例如，用于抑制HIV复制，预防或治疗HIV感染，并用于治疗由此导致的获得性免疫缺陷综合症（AIDS）。
• Discovery of N-(2-aryl-cyclohexyl) substituted spiropiperidines as a novel class of GlyT1 inhibitors
  作者：Emmanuel Pinard、Simona M. Ceccarelli、Henri Stalder、Daniela Alberati

  DOI：10.1016/j.bmcl.2005.09.075

  日期：2006.1

  Screening of the Roche compound library led to the identification of cis-N-(2-phenyt-cyclohexyl)-spiropiperidine 1 as structurally novel GlyT1 inhibitor. The SAR, which was developed in this series, resulted in the discovery of highly potent compounds displaying excellent selectivity against the GlyT2 isoform. (c) 2005 Elsevier Ltd. All rights reserved.
• US7271172B2
  申请人：——

  公开号：US7271172B2

  公开（公告）日：2007-09-18
• US7452992B2
  申请人：——

  公开号：US7452992B2

  公开（公告）日：2008-11-18
• US7569579B2
  申请人：——

  公开号：US7569579B2

  公开（公告）日：2009-08-04