5-cyano-6-dimethylamino-(3,4'-bipyridine)-1'-oxide

• 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-cyano-6-dimethylamino-(3,4'-bipyridine)-1'-oxide
• 英文别名: 3-Cyano-2-dimethylamino-5,4'-bipyridine-1'-oxide；2-(dimethylamino)-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carbonitrile
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: WNMWRLOMJZFXEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Chlor-3-cyan-5-(pyrid-4-yl)pyridin 在 过氧乙酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-cyano-6-dimethylamino-(3,4'-bipyridine)-1'-oxide
  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

• 3-cyano-5,4'-bipyridine-1'-oxide compounds and pharmaceutical
  申请人：Arzneimittelwerk Dresden G.m.b.H.

  公开号：US05162533A1

  公开（公告）日：1992-11-10

  A 3-cyano-5,4'-bipyridine-1'-oxide of the formula ##STR1## and their pharmaceutically acceptable acid addition salts, wherein R is an amino, alkoxy, oxyalkoxy or chloro residue, have heart stimulating cardiotonic and vasodiolatory properties. They can be preparaed by (a) converting an R-substituted-3-cyano-bipyridine to its corresponding N-oxide, or (b) by substituting an R-residue or an R-unsubstituted precursor of the conpound of fomula (i), and if required, converting the product into its pharmaceutically acceptable acid addition salt.

  式子为##STR1##的3-氰基-5,4'-联吡啶-1'-氧化物及其药学上可接受的酸加合物，其中R为氨基，烷氧基，氧烷氧基或氯残基，具有心脏兴奋，心脏强力和血管扩张的特性。它们可以通过以下方法制备：(a)将R-取代的3-氰基联吡啶转化为相应的N-氧化物，或(b)通过取代R残基或未取代的化合物前体，必要时将产物转化为其药学上可接受的酸加合物。
• US5162533A
  申请人：——

  公开号：US5162533A

  公开（公告）日：1992-11-10
• 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.