2-Chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carboxamide | 156032-98-3

• 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: 2-Chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carboxamide
• CAS: 156032-98-3
• 化学式: C₁₁H₈ClN₃O₂
• 分子量: 249.656
• InChiKey: FQODGFWCTUAWTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carboxamide 、 3-二乙胺基丙胺 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and cardiotonic activity of 6-substituted 5-cyano-(3,4′-bipyridine)-1′-oxides and related compounds: molecular structure of 5-cyano-6-morpholino-(3,4′-bipyridine)-1′-oxide (AWD 122–239)

  摘要：

  6-Chloro-3,4'-bipyridine-1-oxides 5 and 5-cyano-1,6-dihydro-2-methyl-6-oxo-3,4'-bipyridine-1'-oxide 7 have been prepared from the corresponding pyridine derivatives by oxidation using peracetic acid. Reaction of 5 with various amines gave the 6-substituted compounds 6. Some of the synthesized products 6 were subsequently converted by derivation into related analogues 8, 9 and 10. In this series 5-cyano-6-morpholino-(3,4'-bipyridine)-1'-oxide (AWD 122-239, 6a), exhibited remarkable positive inotropic potency in spontaneously beating isolated guinea-pig atria as well as in anesthetized pigs. Additionally, 6a showed nearly no inhibition of cyclic AMP phosphodiesterase III. The molecular and crystal structures were determined together with the molecular electrostatic potential and structure-activity relationships are discussed. The obtained results clearly indicate compound 6a as a new type of cardiotonic.

  DOI：

  10.1016/0223-5234(94)90035-3
• 作为产物：
  描述：

  3-Carbamoyl-2-chlor-5-(pyrid-4-yl)pyridin 在 过氧乙酸 、 溶剂黄146 作用下， 反应 4.0h， 以86%的产率得到2-Chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carboxamide
  参考文献：
  名称：

  Synthesis and cardiotonic activity of 6-substituted 5-cyano-(3,4′-bipyridine)-1′-oxides and related compounds: molecular structure of 5-cyano-6-morpholino-(3,4′-bipyridine)-1′-oxide (AWD 122–239)

  摘要：

  6-Chloro-3,4'-bipyridine-1-oxides 5 and 5-cyano-1,6-dihydro-2-methyl-6-oxo-3,4'-bipyridine-1'-oxide 7 have been prepared from the corresponding pyridine derivatives by oxidation using peracetic acid. Reaction of 5 with various amines gave the 6-substituted compounds 6. Some of the synthesized products 6 were subsequently converted by derivation into related analogues 8, 9 and 10. In this series 5-cyano-6-morpholino-(3,4'-bipyridine)-1'-oxide (AWD 122-239, 6a), exhibited remarkable positive inotropic potency in spontaneously beating isolated guinea-pig atria as well as in anesthetized pigs. Additionally, 6a showed nearly no inhibition of cyclic AMP phosphodiesterase III. The molecular and crystal structures were determined together with the molecular electrostatic potential and structure-activity relationships are discussed. The obtained results clearly indicate compound 6a as a new type of cardiotonic.

  DOI：

  10.1016/0223-5234(94)90035-3

文献信息

• Synthesis and cardiotonic activity of 6-substituted 5-cyano-(3,4′-bipyridine)-1′-oxides and related compounds: molecular structure of 5-cyano-6-morpholino-(3,4′-bipyridine)-1′-oxide (AWD 122–239)
  作者：E Klauschenz、V Hagen、B Wiesner、A Hagen、G Reck、EG Krause

  DOI：10.1016/0223-5234(94)90035-3

  日期：1994.1

  6-Chloro-3,4'-bipyridine-1-oxides 5 and 5-cyano-1,6-dihydro-2-methyl-6-oxo-3,4'-bipyridine-1'-oxide 7 have been prepared from the corresponding pyridine derivatives by oxidation using peracetic acid. Reaction of 5 with various amines gave the 6-substituted compounds 6. Some of the synthesized products 6 were subsequently converted by derivation into related analogues 8, 9 and 10. In this series 5-cyano-6-morpholino-(3,4'-bipyridine)-1'-oxide (AWD 122-239, 6a), exhibited remarkable positive inotropic potency in spontaneously beating isolated guinea-pig atria as well as in anesthetized pigs. Additionally, 6a showed nearly no inhibition of cyclic AMP phosphodiesterase III. The molecular and crystal structures were determined together with the molecular electrostatic potential and structure-activity relationships are discussed. The obtained results clearly indicate compound 6a as a new type of cardiotonic.