T3P-Promoted Synthesis of a Series of 2-Aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones and Their Activity against the Kinetoplastid Parasite Trypanosoma brucei

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dc.contributor.authorSilverberg, Lee J.en
dc.contributor.authorMal, Tapas K.en
dc.contributor.authorPacheco, Carlos N.en
dc.contributor.authorPovelones, Megan L.en
dc.contributor.authorMalfara, Madeline F.en
dc.contributor.authorLagalante, Anthony F.en
dc.contributor.authorOlsen, Mark A.en
dc.contributor.authorYennawar, Hemant P.en
dc.contributor.authorSobhi, Hany F.en
dc.contributor.authorBaney, Kayla R.en
dc.contributor.authorBozeman, Robin L.en
dc.contributor.authorEroh, Craig S.en
dc.contributor.authorFleming, Michael J.en
dc.contributor.authorGarcia, Tracy L.en
dc.contributor.authorGregory, Casey L.en
dc.contributor.authorHahn, Julia E.en
dc.contributor.authorHatter, Alyssa M.en
dc.contributor.authorJohns, Lexi L.en
dc.contributor.authorKlinger, Tianna L.en
dc.contributor.authorLi, Jennie J.en
dc.contributor.authorMenig, Andrew J.en
dc.contributor.authorMuench, Grace C.en
dc.contributor.authorRamirez, Melissa E.en
dc.contributor.authorReilly, Jordynen
dc.contributor.authorSacco, Nicoleen
dc.contributor.authorSheidy, Alexandra M.en
dc.contributor.authorStoner, Marla M.en
dc.contributor.authorThompson, Eric N.en
dc.contributor.authorYazdani, Soroush F.en
dc.date.accessioned2021-10-13T12:29:30Zen
dc.date.available2021-10-13T12:29:30Zen
dc.date.issued2021-10-09en
dc.date.updated2021-10-12T14:18:24Zen
dc.description.abstractA series of fourteen 2-aryl-3-phenyl-2,3-dihydro-4<i>H</i>-pyrido[3,2-<i>e</i>][1,3]thiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of <i>N</i>-phenyl-<i>C</i>-aryl imines with thionicotinic acid, two difficult substrates. The reactions were operationally simple, did not require specialized equipment or anhydrous solvents, could be performed as either two or three component reactions, and gave moderate–good yields as high as 63%. This provides ready access to <i>N</i>-phenyl compounds in this family, which have been generally difficult to prepare. As part of the study, the first crystal structure of neutral thionicotinic acid is also reported, and showed the molecule to be in the form of the thione tautomer. Additionally, the synthesized compounds were tested against <i>T. brucei,</i> the causative agent of Human African Sleeping Sickness. Screening at 50 µM concentration showed that five of the compounds strongly inhibited growth and killed parasites.en
dc.description.versionPublished versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationSilverberg, L.J.; Mal, T.K.; Pacheco, C.N.; Povelones, M.L.; Malfara, M.F.; Lagalante, A.F.; Olsen, M.A.; Yennawar, H.P.; Sobhi, H.F.; Baney, K.R.; Bozeman, R.L.; Eroh, C.S.; Fleming, M.J.; Garcia, T.L.; Gregory, C.L.; Hahn, J.E.; Hatter, A.M.; Johns, L.L.; Klinger, T.L.; Li, J.J.; Menig, A.J.; Muench, G.C.; Ramirez, M.E.; Reilly, J.; Sacco, N.; Sheidy, A.M.; Stoner, M.M.; Thompson, E.N.; Yazdani, S.F. T3P-Promoted Synthesis of a Series of 2-Aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones and Their Activity against the Kinetoplastid Parasite Trypanosoma brucei. Molecules 2021, 26, 6099.en
dc.identifier.doihttps://doi.org/10.3390/molecules26206099en
dc.identifier.urihttp://hdl.handle.net/10919/105280en
dc.language.isoenen
dc.publisherMDPIen
dc.rightsCreative Commons Attribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en
dc.subjectpyridothiazinoneen
dc.subjectT3Pen
dc.subjectimineen
dc.subjectN-arylen
dc.subjectthionicotinic aciden
dc.subjectparasitesen
dc.subjectT. bruceien
dc.titleT3P-Promoted Synthesis of a Series of 2-Aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones and Their Activity against the Kinetoplastid Parasite Trypanosoma bruceien
dc.title.serialMoleculesen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten

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