The 12th International Drug Chemistry Congress, Antalya, Turkey, 7 - 10 March 2024, pp.155
Chalcones, found in plants, are
characterized by open-chain structures that incorporate 1,3-diaryl groups
linked to a three-carbon α,β-unsaturated carbonyl structure.1
Chalcones, with their diverse biological activities, play a crucial role in
various pharmacological applications such as the development of novel drugs and
therapeutic agents. Triazoles, a significant class of azole compounds, have
become more accessible in the literature, largely due to the Click chemistry
method pioneered by Sharples.The structural resem blance of this skeletal
configuration to peptide bonds has facilitated extensive exploration,
particularly in the field of medicinal chemistry.Upon examining the literature
featuring these crucial skeletal structures, it was reported that Triazole
chalcone hybrid molecules exhibited effective in vivo studies.2 In
line with this literature insight, firstly 1,4,5-trisubstituted-1,2,3-triazoles
were synthesized, and then triazole-chalcone hybrid molecules containing the
chalcone skeleton on structure from the 1-position of the 1,2,3-triazole.
Notably, the targeted 1,2,3-triazole- chalcone hybrid molecules were
synthesized with high yields, obviating the need for a metal catalyst and avoid
in purification techniques like column chromatography. In this study, we
synthesized 14 new chalcone-1,2,3-triazole hybrid molecules that we think may
exhibit biological effective properties. For this aim first of all,
4-acetylphenzylazide compound was synthesized from 4-acetylaniline and then
4-acetylphenzylazide reacted with benzaldehyde 1a-k using the Claisen-Schmidt
method gave 1-(4-azidophenyl)-3-phenlyprop-2-en-1-ones. After that [3+2] cycloaddition
of this compound with dimethyl acetylenedicarboxylate gave target molecules
dimethyl 1-(4-cinnamoylphenyl)-1H-1,2,3-triazole-4,5-dicarboylate
between 24-79% yields. The structures of all new synthesized compounds were
characterized using IR, 1 H and 13 CNMR spectroscopic
methods.