Show simple item record

dc.contributor.authorColombo, C
dc.contributor.authorPinto, BM
dc.contributor.authorBernardi, A
dc.contributor.authorBennet, AJ
dc.date.accessioned2021-10-12T01:13:36Z
dc.date.available2021-10-12T01:13:36Z
dc.date.issued2016
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/c6ob00999a
dc.identifier.urihttp://hdl.handle.net/10072/408854
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.description.peerreviewedYes
dc.languageeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofpagefrom6539
dc.relation.ispartofpageto6553
dc.relation.ispartofissue27
dc.relation.ispartofjournalOrganic and Biomolecular Chemistry
dc.relation.ispartofvolume14
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
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
dc.date.updated2021-10-12T01:12:12Z
gro.hasfulltextNo Full Text
gro.griffith.authorPinto, Mario M.


Files in this item

FilesSizeFormatView

There are no files associated with this item.

This item appears in the following Collection(s)

  • Journal articles
    Contains articles published by Griffith authors in scholarly journals.

Show simple item record