Hyaluronidase Inhibitory Activity and In Silico Docking Study of New Eugenol 1,2,3-triazole Derivatives

Chemical transformation study is considered as an important tool for new drugs discovery. It was conducted on the natural compound eugenol for semi-synthesizing new structural scaffolds. Three new eugenol 1,2,3-triazole derivatives as well as a known one were synthesized via click chemistry using the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition method. All derivatives were characterized by NMR analysis in combination with ESIMS. Molecular docking and in vitro inhibition potency of eugenol and its derivatives towards hyaluronidase enzyme were examined. The synthesized derivative 4-((4-allyl-2-methoxyphenoxy)methyl)-1-benzyl-1H-1,2,3-triazole showed an enhanced hyaluronidase inhibitory effect, 1.5 times, higher than its parent compound eugenol.

Automated summary

Chemical transformation study is an important tool for new drugs discovery. In this study, new eugenol 1,2,3-triazole derivatives were synthesized via click chemistry using the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition method. Their inhibitory effects on hyaluronidase enzyme were examined, and one derivative showed enhanced inhibitory effect compared to its parent compound eugenol.