6-chloro-5-cyano-(3,4'-bipyridine)-1'-oxide | 137371-41-6

• 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: 6-chloro-5-cyano-(3,4'-bipyridine)-1'-oxide
• 英文别名: 2-chloro-3-cyano-5,4'-bipyridine-1'-oxide；2-chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carbonitrile
• CAS: 137371-41-6
• 化学式: C₁₁H₆ClN₃O
• 分子量: 231.641
• InChiKey: QLJNHAQMRLVCLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-5-cyano-(3,4'-bipyridine)-1'-oxide 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 9-cyano-3,4-dihydro-7-(4-pyridinyl)-2H-pyrido<1,2-a>pyrimidine-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
• 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， 反应 4.0h， 以85%的产率得到6-chloro-5-cyano-(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盐，其中R是氨基、烷氧基、氧烷氧基或氯残基，具有心脏兴奋、强心和血管扩张的特性。它们可以通过（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fomula（i）化合物的R残基或未取代的R前体，并在必要时将产物转化为其药学上可接受的酸盐来制备。
• 3-Cyan-5,4'-oxide, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung
  申请人：ARZNEIMITTELWERK DRESDEN GmbH

  公开号：EP0445552A1

  公开（公告）日：1991-09-11

  3-Cyan-5,4'-bipyridin-1'-oxide, 3-Cyan-5,4'-bipyridine, 2-Chlor-3-cyan-5,4'-bipyridin-1'-oxide, kardioton, vasodilatatorisch 3-Cyan-5,4'-bipyridin-1'-oxide der allgemeinen Formel I und ihre physiologisch verträglichen Säureadditionsalze besitzen wertvolle kardiotone und vasodilatatorische Eigenschaften. Sie können dadurch hergestellt werden, daß man entweder a) 3-Cyan-5,4'-bipyridine der Formel II mit zur Erzeugung von Pyridin-N-oxiden geeigneten Reagenzien, vorzugsweise Persäuren oder Wasserstoffsuperoxid, umsetzt oder b) 2-Chlor-3-cyan-5,4'-bipyridin-1'-oxide der Formel III mit einer Verbindung der Formel IV umsetzt und die erhaltenen Verbindungen der Formel 1 erwünschtenfalls mit physiologisch verträglichen anorganischen oder organischen Säuren in ihre Säureadditionssalze überführt.

  3-氰基-5,4'-联吡啶-1'-氧化物，3-氰基-5,4'-联吡啶，2-氯-3-氰基-5,4'-联吡啶-1'-氧化物，强心剂，血管扩张剂 通式 I 的 3-氰基-5,4'-联吡啶-1'-氧化物及其生理相容的酸加成盐具有重要的强心和血管扩张特性。它们可以通过以下两种方法制备 a) 将式 II 的 3-氰基-5,4'-联吡啶与适用于生产吡啶 N-氧化物的试剂（最好是过酸或过氧化氢）反应，或 b) 式 III 的 2-氯-3-氰基-5,4'-联吡啶-1'-氧化物与式 IV 的化合物反应 如果需要，用生理上相容的无机酸或有机酸将得到的式 1 化合物转化为它们的酸加成盐。
• 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.