2-<2-(dimethylamino)ethenyl>-1,6-dihydro-6-oxo-3-pyridinecarbonitrile | 105276-93-5

• 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: 2-<2-(dimethylamino)ethenyl>-1,6-dihydro-6-oxo-3-pyridinecarbonitrile
• 英文别名: 2-[2-(Dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile；2-[2-(dimethylamino)ethenyl]-6-oxo-1H-pyridine-3-carbonitrile
• CAS: 105276-93-5
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: XLODPSXDXUMZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(dimethylamino)ethenyl>-1,6-dihydro-6-oxo-3-pyridinecarbonitrile 在 N-甲基吡咯烷酮 、 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-(4-Methyl-pyrazol-1-yl)-1H-[1,6]naphthyridin-2-one
  参考文献：
  名称：

  Novel cAMP PDE III inhibitors: 1,6-naphthyridin-2(1H)-ones

  摘要：

  Two series of medorinone (3) analogs were prepared by modifications at C(2) and C(5). The C(2)-series was prepared from 2-chloro-5-methyl-1,6-naphthyridine (4) by replacement of the chloro group with various nucleophiles. The C(5)-series was prepared from 5-acyl-6-[2-(dimethylamino)ethenyl]-2-(1H)-pyridinone (11), 5-bromo-1,6-naphthyridin-2(1H)-one (17), and 1,3-diketones 19 and 27. 1,6-Naphthyridin-2(1H)-ones are novel inhibitors of cAMP PDE III. Modification of the carbonyl group of 3 or N-methylation at N(1) resulted in a dramatic loss of enzyme activity. Absence of the C(5)-methyl group of medorinone (3) or its shift to C(3) or C(7) also resulted in reduced activity. Substitution at C(3) also diminished activity. However, substitution at C(5) by a wide variety of substituents led to improvement of enzyme activity and several C(5)-substituted analogs were more potent than milrinone.

  DOI：

  10.1021/jm00104a012
• 作为产物：
  描述：

  Bredereck 试剂 、 3-氰基-6-羟基-2-甲基吡啶 在 乙醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 以to yield 8.2 g of 2-[2-(dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrile, m.p. 298°-300° C.的产率得到2-<2-(dimethylamino)ethenyl>-1,6-dihydro-6-oxo-3-pyridinecarbonitrile
  参考文献：
  名称：

  1,6-naphthyridine-2(1H)-ones and their use as cardiotonic agents

  摘要：

  5-X-7-R'-1,6-萘啶并[2,1-d]嘧啶-2-酮（式II）或其盐，其中X为溴、氯或肼基，R'为氢或甲基，可用作心脏强效剂。

  公开号：

  US04657915A1