220168-50-3Relevant academic research and scientific papers
A comparison of the reactivity and mutagenicity of n-(benzoyloxy)-n-(benzyloxy)benzamides
Glover, Stephen A.,Hammond, Gerard P.,Bonin, Antonio M.
, p. 9684 - 9689 (1998)
A new series of N-(acyloxy)-N-alkoxybenzamides, AT-(benzoyloxy)-JV-(benzyloxy)benzamides 7 have been synthesized and have been found to be direct acting mutagens in Salmonella TA100. They undergo AAl1 solvolysis to give N-benzoyl-N-(benzyloxy)nitrenium ions 3 under conditions of acid catalysis as well as unusual BAl2 reactions at nitrogen with hydroxide. The latter process affords as intermediates the anomeric hydroxamic esters 4 which rearrange intramolecularly to esters in a HERON reaction. Rates of acid-catalyzed solvolysis and reaction with hydroxide ions correlate with Hammett σ values with low sensitivity (ρ = +0.32 and +0.55, respectively) in accordance with the AAl1 and BAl2 mechanisms. Mutagenicity for the series also appears to correlate with Hammett σ values but with low, negative sensitivity (p = -0.57), and their biological activity may be attributable to their stability under conditions of the Ames assay and hydrophobic binding to DNA, rather than their chemical reactivity.
