TY - JOUR
T1 - Step-by-step synthetic route to access eugenol-1,2,3-triazole-chalcone hybrid
AU - Ullah, Atta
AU - Ardiansah, Bayu
AU - Cahyana, Antonius Herry
AU - Ali, Abad
N1 - Publisher Copyright:
© 2024 The Authors
PY - 2024/12
Y1 - 2024/12
N2 - Molecular hybridization represents a strategic approach in drug design, where two or more pharmacophoric elements from distinct bioactive molecules are integrated into a single hybrid compound. In this study, we synthesized hybrid compounds of chalcone, triazole, and eugenol through straightforward reactions using 4-hydroxyacetophenone as the starting material. Initially, 4-hydroxyacetophenone (1) underwent alkylation with 1,4-dibromobutane to produce compound 2 with an 84 % yield. Compound 2 was then subjected to azidation, resulting in azidobutoxyacetophenone 3 with a 71 % yield. Subsequently, compound 3 was reacted with either benzaldehyde or 4-methoxybenzaldehyde via base-catalyzed aldol condensation, yielding azidobutoxychalcones 4a (69 %) and 4b (84 %). Finally, azide-alkyne [3+2] cycloaddition between 4a/4b and propargylated eugenol afforded chalcone derivatives bearing eugenol-1,2,3-triazole hybrids 5a and 5b, each with a 90 % yield. • Synthesized chalcones featuring an eugenol-1,2,3-triazole scaffold using 4-hydroxyacetophenone as the starting material. • Synthesis was accomplished through a four-step reaction sequence. • Products were obtained in good yield.
AB - Molecular hybridization represents a strategic approach in drug design, where two or more pharmacophoric elements from distinct bioactive molecules are integrated into a single hybrid compound. In this study, we synthesized hybrid compounds of chalcone, triazole, and eugenol through straightforward reactions using 4-hydroxyacetophenone as the starting material. Initially, 4-hydroxyacetophenone (1) underwent alkylation with 1,4-dibromobutane to produce compound 2 with an 84 % yield. Compound 2 was then subjected to azidation, resulting in azidobutoxyacetophenone 3 with a 71 % yield. Subsequently, compound 3 was reacted with either benzaldehyde or 4-methoxybenzaldehyde via base-catalyzed aldol condensation, yielding azidobutoxychalcones 4a (69 %) and 4b (84 %). Finally, azide-alkyne [3+2] cycloaddition between 4a/4b and propargylated eugenol afforded chalcone derivatives bearing eugenol-1,2,3-triazole hybrids 5a and 5b, each with a 90 % yield. • Synthesized chalcones featuring an eugenol-1,2,3-triazole scaffold using 4-hydroxyacetophenone as the starting material. • Synthesis was accomplished through a four-step reaction sequence. • Products were obtained in good yield.
KW - 1,2,3-Triazole
KW - 4-Hydroxyacetophenone
KW - Chalcone
KW - Eugenol
KW - Molecular hybrid
UR - http://www.scopus.com/inward/record.url?scp=85204237323&partnerID=8YFLogxK
U2 - 10.1016/j.mex.2024.102956
DO - 10.1016/j.mex.2024.102956
M3 - Article
AN - SCOPUS:85204237323
SN - 2215-0161
VL - 13
JO - MethodsX
JF - MethodsX
M1 - 102956
ER -