Bassini, Emanuele Gazzotti, Stefano Sannio, Filomena Lo Presti, Leonardo Sgrignani, Jacopo Docquier, Jean-Denis Grazioso, Giovanni Silvani, Alessandra 2020-05-12 The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers–three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free β-aminoboronic acids, quantitatively recovered through basic mild deprotection, were found to be quite stable and were fully characterized, including by 11B-NMR spectroscopy. Single-crystal X-ray diffraction analysis, applied both to a MIDA-protected and a free β-aminoboronic acid derivative, provided evidence for different conformations in the solid-state. Finally, the antimicrobial activities of selected compounds were evaluated by measuring their minimal inhibitory concentration (MIC) values, and the binding mode of the most promising derivative on OXA-23 class D β-lactamase was predicted by a molecular modeling study. application/pdf https://susi.usi.ch/global/documents/319214 https://n2t.net/ark:/12658/srd1319214 https://susi.usi.ch/documents/319214/files/sgrignani_antibiotics_2020.pdf eng info:eu-repo/semantics/altIdentifier/doi/10.3390/antibiotics9050249 info:eu-repo/semantics/altIdentifier/ark/12658/srd1319214 info:eu-repo/semantics/openAccess CC BY Antibiotics. - 2020, vol. 9, no. 5, p. 21 p Multicomponent reactions β-amino boronic acids β-lactamases Covalent docking info:eu-repo/classification/udc/615 Isonitrile-based multicomponent synthesis of β-amino boronic acids as β-lactamase inhibitors http://purl.org/coar/resource_type/c_6501