(S)-2-Allyl-2,3-dihydro-1H-pyridin-4-one | 276699-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-Allyl-2,3-dihydro-1H-pyridin-4-one
• 英文别名: (2S)-2-prop-2-enyl-2,3-dihydro-1H-pyridin-4-one
• CAS: 276699-83-3
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: NGQWPNMTICQZDW-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-Allyl-2,3-dihydro-1H-pyridin-4-one 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
• 作为产物：
  描述：

  4-甲氧基-3-(三异丙基甲硅烷基)嘧啶 、 烯丙基溴化镁 生成 (S)-2-Allyl-2,3-dihydro-1H-pyridin-4-one
  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

• 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.