Triazole is an imperative
heterocycle renowned for its broad-spectrum
biological significance. In this manuscript, facile microwave-assisted
synthesis of a series of 4-(benzylideneamino)-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione 6(a–m) derivatives along with their in
vivo analgesic activity is reported. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanoic
acid (flurbiprofen) was converted to methyl 2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanoate
using microwave irradiation, followed by its hydrazinolysis with hydrazine
monohydrate. 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)propanehydrazide
thus obtained was converted to 4-amino-3-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1H-1,2,4-triazole-5(4H)-thione, followed
by its condensation with different aromatic aldehydes to get the title
compounds. Structures of all the synthesized compounds were established
using different methods (1H NMR and 13C NMR
spectroscopies, mass spectrometry, and elemental analysis) and evaluated
for their potential as analgesic agents by tail flick, hot plate,
and writhing methods. The results of this in vivo study revealed several compounds as potent analgesic agents among
which compound 6e showed significant analgesic effect
for all the three assays employed.