5-[(4-bromophenyl)methyl]-2-methyl-6-oxo-1H-pyridine-3-carbonitrile | 1174930-60-9

• 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: 5-[(4-bromophenyl)methyl]-2-methyl-6-oxo-1H-pyridine-3-carbonitrile
• CAS: 1174930-60-9
• 化学式: C₁₄H₁₁BrN₂O
• 分子量: 303.158
• InChiKey: MDMZTUXXKVRZFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 在 吡啶 、 三乙烯二胺 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 paraffin oil 为溶剂， 反应 0.25h， 生成 5-[(4-bromophenyl)methyl]-2-methyl-6-oxo-1H-pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-pyridone derivatives as inhibitors of phosphodiesterase3 (PDE3): A target for heart failure and platelet aggregation

  摘要：

  Twenty-six 2-pyridone derivatives (8a-8z), which are structurally analogous to amrinone and milrinone two important cardiotonic drugs, are synthesized and characterized. The synthesis of 2-pyridone derivatives involves addition, followed by cyclization between Baylis-Hillman acetates (7a-7k) and enamino esters or nitriles (3a-3e). Thus synthesized pyridones were subjected to PDE3 inhibitory activity, 14 pyridones were found to be hits out of 26 pyridones synthesized and out of 14 hits, there are 5 pyridones found to be lead compounds having excellent PDE3 inhibitory activity. Further we have carried out computational analysis to understand protein/enzyme and 2-pyridone derivative interactions to identify amino acid residues involved in the vicinity of binding and compared with milrinone drug. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.019

文献信息

• Simple, facile and one-pot conversion of the Baylis–Hillman acetates into 3,5,6-trisubstituted-2-pyridones
  作者：Mettu Ravinder、Partha Sarathi Sadhu、Vaidya Jayathirtha Rao

  DOI：10.1016/j.tetlet.2009.04.136

  日期：2009.7

  A facile route for the synthesis of novel 3,5,6-trisubstituted-2-pyridones from the acetylated Baylis-Hillman esters with beta-enamino esters or beta-enamino nitriles in one pot with good yields is described. (C) 2009 Published by Elsevier Ltd.