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dc.contributor.authorColombo, C
dc.contributor.authorPinto, BM
dc.contributor.authorBernardi, A
dc.contributor.authorBennet, AJ
dc.description.abstractThis manuscript describes a novel class of derivatives based on a bicyclo[3.1.0]hexane scaffold, proposed as mimics of sialic acid in a distorted boat conformation that is on the catalytic pathway of neuraminidases (sialidases). A general synthetic route for these constrained-ring molecules was developed using a photochemical reaction followed by a Johnson-Corey-Chaykovsky cyclopropanation. Functionalization with the goal of occupying the 150-cavity was also exploited. Inhibition assays demonstrated low micromolar inhibition against both group-1 (H5N1) and group-2 (H9N2) influenza neuraminidase subtypes, indicating good affinity for the alpha and beta sialic acid mimics and 150-cavity-targeted derivatives. These results provide a validation of a bicyclo[3.1.0]hexane scaffold as a mimic of a distorted sialic acid bound in the neuraminidase active site during catalysis.
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofjournalOrganic and Biomolecular Chemistry
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.titleSynthesis and evaluation of influenza A viral neuraminidase candidate inhibitors based on a bicyclo[3.1.0]hexane scaffold
dc.typeJournal article
dc.type.descriptionC1 - Articles
dcterms.bibliographicCitationColombo, C; Pinto, BM; Bernardi, A; Bennet, AJ, Synthesis and evaluation of influenza A viral neuraminidase candidate inhibitors based on a bicyclo[3.1.0]hexane scaffold, Organic and Biomolecular Chemistry, 2016, 14 (27), pp. 6539-6553
gro.hasfulltextNo Full Text
gro.griffith.authorPinto, Mario M.

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