Synthesis and analgesic activity of a series of new azaalkane bis-guanidinium and bis(2-aminoimidazolinium) compounds

Bioorg Med Chem. 2003 Apr 3;11(7):1283-91. doi: 10.1016/s0968-0896(02)00637-5.

Abstract

In the present paper, we wish to report the synthesis and antinociceptive activity of a series of new azaalkane bis(2-aminoimidazolinium) compounds from which, N,N'-di(4,5-dihydro-1H-imidazol-2-yl)-3-aza-1,6-hexanediamine 2a has shown the best analgesic properties in vivo in two different assays (i.e., acetic acid-induced writhing test and hot-plate test in mice), as well as oral bioavailability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid
  • Analgesics, Non-Narcotic / chemical synthesis*
  • Analgesics, Non-Narcotic / pharmacokinetics
  • Analgesics, Non-Narcotic / pharmacology*
  • Animals
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / pharmacology*
  • Biological Availability
  • Dose-Response Relationship, Drug
  • Guanidine / analogs & derivatives*
  • Guanidine / chemical synthesis*
  • Guanidine / pharmacology*
  • Guinea Pigs
  • Hot Temperature
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology*
  • In Vitro Techniques
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Molecular Conformation
  • Muscle Contraction / drug effects
  • Muscle, Skeletal / drug effects
  • Pain Measurement / drug effects
  • Reaction Time / drug effects
  • Spectrophotometry, Infrared

Substances

  • Analgesics, Non-Narcotic
  • Aza Compounds
  • Imidazoles
  • Indicators and Reagents
  • Guanidine
  • Acetic Acid