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dc.creatorHo, DM
dc.creatorZdilla, MJ
dc.date.accessioned2020-12-16T20:05:15Z
dc.date.available2020-12-16T20:05:15Z
dc.date.issued2018-11-01
dc.identifier.issn2053-2296
dc.identifier.issn2053-2296
dc.identifier.doihttp://dx.doi.org/10.34944/dspace/4599
dc.identifier.other30398206 (pubmed)
dc.identifier.urihttp://hdl.handle.net/20.500.12613/4617
dc.description.abstract© Ho and Zdilla 2018 Tolnaftate, a classic antifungal compound, has been found to crystallize from 1:1 (v/v) acetone–water as large flat colorless needles in the centrosymmetric monoclinic space group P21/c. These crystals contain a 50:50 mixture of the (+ap,−sp,+ac,−ac) and (−ap,+sp,−ac,+ac) conformers. The bond lengths in the central CNOS unit are 1.3444 (19), 1.3556 (18) and 1.6567 (15) Å for C—N, C—O and C—S, respectively, and the CNOS and C3N moieties are flat and nearly coplanar with each other, consistent with the C—N bond possessing partial double-bond character. Tolnaftate and the four most closely related N,N-disubstituted thiocarbamates in the Cambridge Structural Database (CSD) all exist as E-conformational isomers in the solid state. Among these five compounds, tolnaftate is the only one in which the N-tolyl moiety is positioned trans to the S atom, i.e. the N-aryl substituent in each of the other compounds is positioned cis to their respective S atom. Notably, and more importantly, our experimental X-ray structure is unlike all prior theoretical models available for tolnaftate. The implication, either directly or indirectly, is that some of those theoretical models used in earlier studies to explain the spectroscopic properties of tolnaftate and to suggest which protein–ligand interactions are responsible for the binding of tolnaftate to squalene epoxidase are either inappropriate or structurally unreasonable, i.e. the results and conclusions from those prior studies are in need of critical reassessment.
dc.format.extent1495-1501
dc.language.isoeng
dc.relation.haspartActa Crystallographica Section C: Structural Chemistry
dc.relation.isreferencedbyInternational Union of Crystallography (IUCr)
dc.rightsCC BY
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjecttolnaftate
dc.subjecttopical antifungal
dc.subjectsolid-state conformation
dc.subjectcrystal structure
dc.titleThe solid-state conformation of the topical antifungal agent O-naphthalen-2-yl N-methyl-N-(3-methylphenyl)carbamothioate
dc.typeArticle
dc.type.genreJournal Article
dc.relation.doi10.1107/S2053229618013591
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.creator.orcidZdilla, Michael|0000-0003-0212-2557
dc.date.updated2020-12-16T20:05:12Z
refterms.dateFOA2020-12-16T20:05:16Z


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