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Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

2019; Beilstein Institute for the Advancement of Chemical Sciences; Volume: 15; Linguagem: Inglês

10.3762/bjoc.15.247

2195-951X

José Brango‐Vanegas, Luan A. Martinho, Lucinda J. Bessa, Andreanne Gomes Vasconcelos, Alexandra Plácido, Alex Leite Pereira, J. R. Leite, Angelo H. L. Machado,

Peptidase Inhibition and Analysis

Eight new sulfide-based cyclic peptidomimetic analogues of solonamides A and B have been synthesized via solid-phase peptide synthesis and SN2' reaction on a Morita-Baylis-Hillman (MBH) residue introduced at the N-terminal of a tetrapeptide. This last step takes advantage of the electrophilic feature of the MBH residue and represents a new cyclization strategy occurring. The analogues were prepared in moderate overall yields and did not show toxic effects on Staphylococcus aureus growth and were not toxic to human fibroblasts. Two of them inhibited the hemolytic activity of S. aureus, suggesting an interfering action in the bacterial quorum sensing similar to the one already reported for solonamides.