Antiprotozoal thiazoles. 2. 2 (5 Nitro 2 furyl-, thiazolyl-, and 1 methylimidazolyl-)thiazoles

Article abstract of DOI:10.1021/jm00217a017

Ten 2 substituted 4 thiazolecarboxaldehyde hydrazones bearing 5 nitro 2 furyl, 5 nitro 2 thiazolyl, and 1 methyl 5 nitro 2 imidazolyl functions have been prepared and screened for activity against Trypanosoma cruzi infections in mice. The results permitted the ranking of these substituents in decreasing order of activity: 1 methyl 5 nitro 2 imidazolyl > 5 nitro 2 furyl > 5 nitro 2 thiazolyl, the last being inactive. Some structural features of the side chain necessary for optimum activity are discussed. The most active compound, 4 [[[2 (1 methyl 5 nitro 2 imidazolyl) 4 thiazolyl]methylene]amino]thiomorpholine 1,1 dioxide, compared favorably with the standard Nifurtimox against 3 recent clinical isolates of T. cruzi, including 1 with a high myocardial tissue infiltration.