title: Rifamycins: modulation of specific anti-poxviral activity by small substitutions on the piperazinyliminomethyl side chain.
abstract: Rifamycin derivatives differing in the substitutent at the 4 position of the piperazinyliminomethyl side chain were tested for anti-poxviral activity. The effects of each derivative on wild-type vaccinia virus and on a mutant selected for resistance to rifampin were determined. Antiviral activity was measured in tissue culture by plaque inhibition, reduction in virus yield, and specific interruption of virus morphogenesis. Rifamycin derivatives containing H, ethyl, or propyl groups at the 4 position of the piperazinyliminomethyl side chain were much less active than rifampin, which has a methyl group at this position. Thus, minimal shortening or lengthening of the methyl piperazinyliminomethyl side chain of rifampin led to loss of specific antiviral activity. In contrast, the derivative containing an amino group at the 4 position of the piperazinyliminomethyl side chain had enhanced anti-poxviral activity.
mesh_terms: D007097:Imines / Q000494:pharmacology; D010879:Piperazines / Q000494:pharmacology*; D011212:Poxviridae / Q000187:drug effects*; D012294:Rifamycins / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D010948:Viral Plaque Assay
chemical_list: D007097:Imines; D010879:Piperazines; D012294:Rifamycins