Purpose: To synthesize and
characterize palmitoyl amino benzamides, and to evaluate
them for possible anti-inflammatory and anti-nociceptive
activities.
Methods: Palmitoyl amino benzamides
were synthesized by the opening of isatoic anhydride
ring with respective amino acids (glycine, β-alanine and
γ-aminobutyric acid) and the condensation of the product
with palmitoyl chloride. The final products were
purified on column chromatography, eluting with
dichloromethane/ethyl acetate. All the compounds were
unequivocally characterized using the combination of
infra red (IR), 1H and 13C (nuclear magnetic resonance (NMR),
mass spectrometry (MS) and elemental analysis. In vivo
anti-inflammatory and anti-nociceptive activities of the
synthesized compounds at 20, 50 and 100mg/kg doses were
carried out using carrageenan-induced paw oedema in rat
and acetic acid-induced writhing in mice, respectively.
Aspirin was used at a dose of 100mg/kg as the reference
drug.
Results: The compounds were obtained
in high yield (70 – 90 %) and purity. The
anti-inflammatory results showed a poor activity for the
compounds except o-palmitoylamino N-carboxyethyl
benzamide which produced significant inhibition (p <
0.05) at a dose of 50 mg/kg (43.8 % oedema inhibition)
while the reference drug, aspirin, showed 51.3 %
inhibition. The anti-nociceptive study, however, showed
good inhibition (p < 0.05) of acetic acid-induced
writhing, with o-palmitoylamino N-carboxymethylbenzamide
producing 86.2 % inhibition at 100 mg/kg dose compared
with the reference drug (aspirin) which gave 74.3 %
inhibition at 100 mg/kg.
Conclusion: The findings of this study
indicate that the synthesized compounds, though
displaying poor anti-inflammatory activity, do possess
promising anti-nociceptive activity.
Keywords: Anti-inflammatory,
Analgesic, Benzamide, Palmitoyl, Glycine, β-Alanine,
γ-Aminobutyric acid, Aspirin