S(RN)1 synthesis of new 5-nitroimidazoles highly active against protozoa and anaerobes

Article abstract of DOI:10.1016/0223-5234(91)90026-J

1-Methyl-2-chloromethyl-5-nitroimidazole reacts by an S(RN)1 mechanism with various aliphatic, cyclic or heterocyclic nitronate anions to afford, in high yields, new 5-nitroimidazoles bearing a trisubstituted ethylenic double bond at the 2 position. Some of these compounds are as active as metronidazole in vitro and in vivo against protozoa and anaerobic bacteria. Structure-activity relationships are discussed.