(S)-2-Allyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester | 276699-80-0

• 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: (S)-2-Allyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-4-oxo-2-prop-2-enylpiperidine-1-carboxylate
• CAS: 276699-80-0
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: UYFQIJQUASHBEP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Allyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester 在 potassium tert-butylate 、 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 (2S,4R)-2-Allyl-4-(4-amino-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
• 作为产物：
  描述：

  4-甲氧基-3-(三异丙基甲硅烷基)嘧啶 在 4-二甲氨基吡啶 、 溶剂黄146 、 锌 作用下， 以 乙腈 为溶剂， 生成 (S)-2-Allyl-4-oxo-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

文献信息

• Beta-amino acid derivatives as inhibitors of matrix metalloproteases and TNF-alpha
  申请人：——

  公开号：US20040072802A1

  公开（公告）日：2004-04-15

  The present application describes novel &bgr;-amino acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, X, Z, U a , X a , Y a , Z a , R 1 , R 2 , R 3 , R 4 , and R 4a are defined in the present specification, which are useful as metalloprotease and/or as TNF-&agr; inhibitors.

  本申请描述了式I的新颖β-氨基酸衍生物：1或其药用可接受的盐或前药形式，其中A、X、Z、Ua、Xa、Ya、Za、R1、R2、R3、R4和R4a在本规范中有定义，这些衍生物可用作金属蛋白酶和/或TNF-α抑制剂。
• 2,4-Disubstituted piperidines as selective CC chemokine receptor 3 (CCR3) antagonists: Synthesis and selectivity
  作者：Paul S. Watson、Bin Jiang、Kim Harrison、Nao Asakawa、Patricia K. Welch、Maryanne Covington、Nicole C. Stowell、Eric A. Wadman、Paul Davies、Kimberly A. Solomon、Robert C. Newton、George L. Trainor、Steven M. Friedman、Carl P. Decicco、Soo S. Ko

  DOI：10.1016/j.bmcl.2006.08.012

  日期：2006.11

  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.