Brominated analogs of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone: Preparation of 3-chloro-4-(bromochloromethyl)-5-hydroxy-2(5H)-furanone and mutagenicity studies

The brominated hydroxyfuranone structurally related to the potent mutagen M X, namely 3-chloro-4-(bromochloromethyl)-5-hydroxy-2(5H)-furanone (BMX-1), has been synthesized and characterized. The mutagenic activity of this brom ohydroxyfuranone together with those of its analogs BMX-2 and BMX-3 has bee n assessed by employing the Ames test with the Salmonella typhimurium strai ns TA98 and TA100. The mutagenic potencies in TA100 without S9 metabolic ac tivation were 22.05 +/- 3.15 revertants/ng for BMX-1, 28.64 +/- 2.65 revert ants/ng for BMX-2, and 37.29 +/- 5.73 revertants/ng for BMX-3, whereas in t he TA98 strain without metabolic activation, they were six- to ninefold low er. Studies carried out on the stability of these halogenated furanones sug gest that the mutagenic activity observed is more related to the cyclic for m of these derivatives.