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

2 November 2000

journal article
research article
Published by Oxford University Press (OUP) in Environmental Toxicology and Chemistry

Vol. 19 (11) , 2631-2636
https://doi.org/10.1002/etc.5620191103

Abstract

The brominated hydroxyfuranones sructurally related to the potent mutagen MXnamely3‐chloro‐4‐(bromochlorome‐thyl)‐5‐hydroxy‐2(5H)‐furanone (BMX‐1), has been synthesized and characterized. The mutagenic activity of this bromohydro‐xyfuranone together with those of its analogs BMX‐2 and BMX‐3 has been assessed by employing the Ames test with the Salmonella typhimurium strains TA98 and TA100. The mutagenic potencies in TA100 without S9 metabolic activation were 22.05 ± 3.15 revertants/ng for BMX‐1, 28.64 ± 2.65 revertants/ng for BMX‐2, and 37.29 ± 5.73 revertants/ng for BMX‐3, whereas in the TA98 strain without metabolic activation, they were six‐ to ninefold lower. Studies carried out on the stability of these halogenated furanones suggest that the mutagenic activity observed is more related to the cyclic form of these derivatives.

Keywords

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