In search of new active molecules, a small focused library of new 1,2,3-triazoles derived from naphthols were efficiently prepared via the click chemistry approach. The synthesized triazole derivatives were evaluated for their antifungal, antioxidant and antitubercular activities. Furthermore, to rationalize the observed biological activity data, the molecular docking study has also been carried out against the active site of cytochrome P450 lanosterol 14α-demethylase of C. albicans to understand the binding affinity and binding interactions of enzyme and synthesized derivatives, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and In Silico study suggest that the 1,2,3-triazole derivatives may possess the ideal structural requirements for the further development of novel therapeutic agents.