3,5-diacetyl-6-methyl-1H-pyridin-2-one | 59503-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-diacetyl-6-methyl-1H-pyridin-2-one
• 英文别名: 3,5-Diacetyl-6-methyl-2(1H)pyridon；3,5-Diacetyl-6-methyl-2-pyridon；3,5-diacetyl-6-methyl-1H-pyridin-2-one
• CAS: 59503-68-3
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: QWRBTUMJZWASMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酰胺 、 3-dimethylaminomethylenepentane-2,4-dione 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到3,5-diacetyl-6-methyl-1H-pyridin-2-one
  参考文献：
  名称：

  3-Acetyl-5-acylpyridin-2(1H)-ones and 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones: synthesis, cardiotonic activity and computational studies

  摘要：

  A series of milrinone analogues, namely 6-substituted 3-acetyl-5-acylpyridin-2(1H)-ones 4a-c, e, f and 7-substituted or unsubstituted 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones 4g-j, in which the cyano group was replaced by the acetyl function, was prepared. In a preliminary pharmacological investigation on spontaneously beating atria from reserpine-treated guinea-pigs, all new compounds did not induce any inotropic effect equivalent or higher than that of the milrinone chosen as the reference compound. In order to rationalise how the structure modifications influence the activity and the selectivity of the title compounds, a computational study has been performed. The important role of the substituents in position-3 and -6 on the pyridone nucleus has been highlighted. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00053-1

文献信息

• 3-Acetyl-5-acylpyridin-2(1H)-ones and 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones: synthesis, cardiotonic activity and computational studies
  作者：Eleonora Lo Presti、Raffaella Boggia、Antonio Feltrin、Giulia Menozzi、Paola Dorigo、Luisa Mosti

  DOI：10.1016/s0014-827x(99)00053-1

  日期：1999.7

  A series of milrinone analogues, namely 6-substituted 3-acetyl-5-acylpyridin-2(1H)-ones 4a-c, e, f and 7-substituted or unsubstituted 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones 4g-j, in which the cyano group was replaced by the acetyl function, was prepared. In a preliminary pharmacological investigation on spontaneously beating atria from reserpine-treated guinea-pigs, all new compounds did not induce any inotropic effect equivalent or higher than that of the milrinone chosen as the reference compound. In order to rationalise how the structure modifications influence the activity and the selectivity of the title compounds, a computational study has been performed. The important role of the substituents in position-3 and -6 on the pyridone nucleus has been highlighted. (C) 1999 Elsevier Science S.A. All rights reserved.