Cheah et al. have reported the synthesis of antibacterial peptidometics via ring opening of N-acetylisatins with amino acid methyl esters (or methyl esters of di- and tri-peptides) to produce glyoxylamides (Tetrahedron Lett. 2008 , 49, 2965-2968; Tetrahedron 2011 , 67, 7603-7610). N-Acylisatins are more reactive in this manner than are the corresponding isatins themselves as the C2 carbonyl moiety of the former behaves as an imide carbonyl as opposed to the conventional amide carbonyl of the latter. We are using Suzuki-derived 6-(aryl)-N-acetylisatins and amino acid methyl esters to prepare new mono-glyoxylamide peptidomimetics for antibacterial assays.

Synthesis of novel glyoxylamides via reaction of 6-aryl-<i>N</i>-acetylisatins with amino acid methyl esters

247th National Meeting (2014)

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Synthesis of novel glyoxylamides via reaction of 6-aryl-N-acetylisatins with amino acid methyl esters