2-(4-Amino-butyl)-4-benzyl-piperidine-1-carboxylic acid tert-butyl ester | 915379-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(4-Amino-butyl)-4-benzyl-piperidine-1-carboxylic acid tert-butyl ester
• CAS: 915379-54-3
• 化学式: C₂₁H₃₄N₂O₂
• 分子量: 346.513
• InChiKey: PHOHVWNTHYKRKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-Amino-butyl)-4-benzyl-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[4-((2R,4S)-4-Benzyl-piperidin-2-yl)-butyl]-3-(3-cyano-phenyl)-urea
  参考文献：
  名称：

  2,4-Disubstituted piperidines as selective CC chemokine receptor 3 (CCR3) antagonists: Synthesis and selectivity

  摘要：

  Linear unselective CCR3 antagonist leads with IC50 values in the 200 nM range were converted into low nM binding compounds selective at CCR3 by moving the piperidine nitrogen substituent to the carbon at the 2-position of the ring. Substitution of the piperidine nitrogen with simple alkyl and acyl groups was found to improve the selectivity of this new compound class. In particular, N-{3-[(2S, 4R)-1-(propyl)-4-(4-fluorobenzyl)piperidinyl]propyl}-N'-(3-acetylphenyl)urea exhibited single digit nanomolar IC50 values for CCR3 with > 100-fold selectivity against an extensive counter screen panel. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.012
• 作为产物：
  描述：

  tert-butyl 4-benzylpiperidine-1-carboxylate 在 palladium on activated charcoal 吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 氢气 、 仲丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 生成 2-(4-Amino-butyl)-4-benzyl-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  2,4-Disubstituted piperidines as selective CC chemokine receptor 3 (CCR3) antagonists: Synthesis and selectivity

  摘要：

  Linear unselective CCR3 antagonist leads with IC50 values in the 200 nM range were converted into low nM binding compounds selective at CCR3 by moving the piperidine nitrogen substituent to the carbon at the 2-position of the ring. Substitution of the piperidine nitrogen with simple alkyl and acyl groups was found to improve the selectivity of this new compound class. In particular, N-{3-[(2S, 4R)-1-(propyl)-4-(4-fluorobenzyl)piperidinyl]propyl}-N'-(3-acetylphenyl)urea exhibited single digit nanomolar IC50 values for CCR3 with > 100-fold selectivity against an extensive counter screen panel. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.012