Eighteen coumarin derivatives were tested as inhibitors of oxidosqualene cyclases (OSCs) from Saccharomyces cerevisiae, Trypanosoma cruzi, Pneumocystis carinii, Homo sapiens, and Arabidopsis thaliana, all expressed in an OSC-defective strain of S. cerevisiae.35 All the compounds have an aminoalkyl chain bound to an aromatic nucleus; unconventional synthetic procedures (microwave- and ultrasound-promoted reactions) were successfully used to prepare some of them. The most interesting structure-dependent difference in inhibitory activities was observed with an N-oxide group replacement of the tertiary amino group at the end of the side chain. An interesting species specificity also emerged: T. cruzi OSC was the least sensitive enzyme; P. carinii and A. thaliana OSCs were the most sensitive. The remarkable activities of three compounds on the T. cruzi enzyme and of five of them on the P. carinii enzyme suggest the present series as a promising compound family for the development of novel antiparasitic agents.