Investigations on the synthesis and properties of N-phenyl derivatives of 1,4-dioxo(1,4,5-trioxo)-1,2,3,4-tetra(1,2,3,4,5,6-hexa) hydropyrido-[3,4-d]pyridazines and allied compounds

Farmaco. 1998 Jul 30;53(7):468-74. doi: 10.1016/s0014-827x(98)00050-0.

Abstract

2-(1-Piperidino)- and 2-(4-methyl-1-piperazinyl)-6-methyl-3,4-pyridinedicarboximides (1, 2) react with N-phenylhydrazine yielding N-phenylamino-3,4-pyridinedicarboximides (7, 8). The same reaction with 1,6-dimethyl-2-oxo-1,2-dihydro- and 2-chloro-6-methyl-3,4-pyridinedicarboximides (3, 17) gives the salts of the corresponding N-phenylpyridopyridazines with phenylhydrazine (13, 18), which transform into N-phenylaminoimides (14, 19) during boiling in 80% acetic acid. Compounds 7, 8 and 14 isomerize to the corresponding 2-phenyl-1,4-dioxo(1,4,5-trioxo)-1,2,3,4-tetra(1,2,3,4,5,6-hexa) hydropyrido[3,4-d]pyridazines (9, 10, 15) under the influence of heating in alcoholic solution of C2H5ONa or CH3ONa. Only in the case of imide 19 are 2- and 3-phenyl isomers (20 and 21) formed under these conditions. Some of the obtained compounds were pharmacologically active.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Female
  • Injections, Intraperitoneal
  • Lethal Dose 50
  • Male
  • Mice
  • Molecular Structure
  • Motor Activity / drug effects
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry*
  • Pyridazines / pharmacology
  • Pyridazines / toxicity
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Pyridazines