Lavendustin A is a natural product isolated from the actinobacteria Streptomyces griseolavendus that presents a potent inhibitory activity on the Epidermal Growth Factor Receptor Protein Tyrosine Kinase (EGFR PTK). In addition, some of its analogues have also shown potent inhibitory activity against the polymerization of tubulin to microtubules, a pivotal process for the cell mitosis. From strategic structural modifications, two useful unprecedented alkynes bearing lavendustin A pharmacophoric subunit were rapidly accessed. Next, a set of novel triazole analogues of lavendustin A were synthesized in good yields employing CuI‐catalyzed azide‐alkyne cycloadditions (CuAAC) under mild conditions. Furthermore, preliminary evaluation of their biological activity against the epimastigote stage of Trypanosoma cruzi points towards promising trypanocidal properties.