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Authordc.contributor.authorGómez, Johana 
Authordc.contributor.authorKlahn, A. Hugo 
Authordc.contributor.authorFuentealba, Mauricio 
Authordc.contributor.authorSierra, Diego 
Authordc.contributor.authorOlea Azar, Claudio
Authordc.contributor.authorMaya Arango, Juan 
Authordc.contributor.authorMedina, Manuela E. 
Cita de ítemdc.identifier.citationJournal of Organometallic Chemistry 839 (2017) 108-115
Abstractdc.description.abstractThe synthesis of unsymmetrical ferrocenyl and cyrhetrenyl azines [(h5-C5H4)-CR¼N-N¼CH-2-C4H2X-5-NO2]M (M¼Re(CO)3, Fe(h5-C5H5); R¼H, CH3,X¼O, S) has led to the development of new derivativesof 5-nitroheterocycles as potential anti-trypanosomal agents. The structures of compounds have beenconfirmed using conventional spectroscopic techniques (FT-IR,1H and13C NMR), mass spectrometry,including single-crystal X-ray diffraction analysis of compounds2NTand4NT. Based on the chemicalshifts of the iminic carbons (C6,C7) and the reduction potential of the nitro group (E1/2 NO2), an extensivep-conjugation of the azine bridge (-C(R)¼N-N¼CH-) was observed along with a correlation between theopposing electronic effects of the cyrhetrenyl and ferrocenyl fragments. It was established that the ex-istence of an electron-withdrawing group (cyrhetrene) could facilitate the generation of radical species(RNO2to RNO2 ) through the azine bridge. The organometallic azines were evaluated for anti-trypanosomal activityin vitroagainst the epimastigote form of the Dm28c strain ofT. cruzi, yieldingIC50values in the low micromolar range.
Type of licensedc.rightsAttribution-NonCommercial-NoDerivs 3.0 Chile
Link to Licensedc.rights.uri
Sourcedc.sourceJournal of Organometallic Chemistry
Keywordsdc.subjectChagas disease
Keywordsdc.subjectCyclic voltammetry
Keywordsdc.subjectCyrhetrenyl azines
Keywordsdc.subjectFerrocenyl azines
Keywordsdc.subjectStructural characterization
Keywordsdc.subjectTrypanosoma cruzi
Títulodc.titleFerrocenyl and cyrhetrenyl azines containing a 5-nitroheterocyclic moiety: Synthesis, structural characterization, electrochemistry and evaluation as anti-Trypanosoma cruzi agents
Document typedc.typeArtículo de revista
Indexationuchile.indexArtículo de publicación SCOPUS

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Attribution-NonCommercial-NoDerivs 3.0 Chile
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Chile