N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide | 945980-23-4

• 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: N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
• 英文别名: 2-[4-(1-methyl-6-oxopyridin-3-yl)phenoxy]-N-prop-2-enylacetamide
• CAS: 945980-23-4
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: WIKIZWIITSJUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide 、 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 1,1,2-三氯乙烷 为溶剂， 反应 16.0h， 以30%的产率得到2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049
• 作为产物：
  描述：

  2-氟-5-溴吡啶 在 四(三苯基膦)钯 盐酸 、 氢氧化钾 、 四丁基溴化铵 、 氢溴酸 、 lithium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
  参考文献：
  名称：

  Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase

  摘要：

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.049

文献信息

• Evaluation of 4′-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5α-reductase
  作者：Anna R. McCarthy、Rolf W. Hartmann、Andrew D. Abell

  DOI：10.1016/j.bmcl.2007.04.049

  日期：2007.7

  4'-Substituted bicyclic pyridones were prepared and evaluated as non-steroidal inhibitors of type I and 2 steroid 5 alpha-reductase (SR). A range of 4'-substituents were incorporated into the bicyclic scaffold to investigate SAR within and across different classes of non-steroidal inhibitors of SR. Bicyclic pyridones containing a 4'-benzoyl or long carbon chain tether showed more potent inhibition against type I SR than inhibitors with N-substituted acetamide groups in the 4'-position. SAR derived from 4'-substituted bicyclic pyridones reported here do not correlate with SAR derived from known potent 4'-substituted biaryl acid SR inhibitors. A 4'-benzoyl group is favoured by the active site in both isozymes. (c) 2007 Elsevier Ltd. All rights reserved.