Some new derivatives of 1,2,4-triazolo[2,3-a]benzimidazoles were synthesized through the reaction of 1,2-diaminobenzimidazole with carbon disulfide. The resulting 1,2,4-triazolo[2,3-a]benzimidazole-2-thione intermediate reacted with one equivalent of the appropriate respective alkyl halide to give the corresponding 2-alkylthio derivative 3a-g. The latters were acylated to afford the 1-acyl-2-alkylthio-1,2,4-triazolo[2,3-a]-benzimidazole derivatives 4-10 in good yields. Structures of the new compounds were verified on the basis of spectral and elemental methods of analyses. Fourteen of the prepared compounds were tested for their possible antifungal activities. Most of the tested compounds showed activity against Candida albicans and Fusarium oxysporum comparable to that of fluconazole as a reference drug. Compounds 8a, 9a, and 10d are the most active ones against most of the used fungi. Compounds 3e, 4d, 5d, 6d, 7d, 8c, 8d, 9d, and 10d were tested for their anti-inflammatory and analgesic effects; most of these compounds showed potent and significant results compared to indomethacin. Moreover, ulcerogenicity and the median lethal dose (LD50) of the most active compound 8d were determined in mice; LD50 was found to be 275 mg kg-1 (i.p.).Sintetizirani su novi derivati 1,2,4-triazolo[2,3-a]benzimidazola reakcijom 1,2-diaminobenzimidazola s ugljičnim disulfidom. Nastali 1,2,4-triazolo[2,3-a]benzimidazol-2-tioni reagiraju s jednim ekvivalentom odgovarajućeg alkil halida pri čemu nastaju 2-alkiltio derivati 3a-g. Acilacijom produkata 3 dobiveni su derivati 1-acil-2-alkiltio-1,2,4-triazolo[2,3-a]-benzimidazola 4-10 u dobrim iskorištenjima. Strukture novih spojeva potvrđene su spektroskopskim metodama i elementarnom analizom. Ispitivano je antimikotsko djelovanje 14 priređenih spojeva, uz flukonazol kao poredbenu tvar. Većina testiranih spojeva djeluje na Candida albicans i Fusarium oxysporum slično kao flukonazol. Najaktivniji su bili spojevi 8a, 9a i 10d. Produkti 3e, 4c, 5c, 6c, 7c, 8b, 8c, 9c i 10c ispitani su na protuupalno i analgetsko djelovanje, uz indometacin kao poredbenu tvar. Većina spojeva ima značajno djelovanje. Najaktivniji spoj testiran je na ulcerogenost. Srednja letalna doza (LD50) određena je na miševima i iznosi 275 mg kg-1 (i.p.)
