Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

Farmaco. 2002 Nov;57(11):897-908. doi: 10.1016/s0014-827x(02)01302-2.

Abstract

Synthesis of 2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives of 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones (8-12) is described. The chlorides used in the above synthesis can exist in two isomeric forms: chain (18-20) and cyclic (19a, 20a). The compounds 8-12 exhibited potent analgesic activity which was superior than that of acetylsalicylic acid in two different tests. Most of the investigated imides suppressed significantly spontaneous locomotor activity in mice.

MeSH terms

  • Analgesics, Non-Narcotic / chemical synthesis*
  • Analgesics, Non-Narcotic / pharmacology*
  • Analgesics, Non-Narcotic / toxicity
  • Animals
  • Blood Pressure / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Female
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Motor Activity / drug effects
  • Pain Measurement / drug effects
  • Piperazines / chemical synthesis*
  • Piperazines / pharmacology*
  • Pyridones / chemical synthesis*
  • Pyridones / pharmacology*
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology*
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship

Substances

  • Analgesics, Non-Narcotic
  • Indicators and Reagents
  • Piperazines
  • Pyridones
  • Pyrroles