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dc.contributor.authorPertejo Fernández, Pablo
dc.contributor.authorGarcía Valverde, María 
dc.contributor.authorPeña Calleja, Pablo 
dc.contributor.authorCordero Tejedor, Nicolás A. 
dc.contributor.authorTorroba Pérez, Tomás 
dc.contributor.authorGonzález Ortega, Alfonso .
dc.date.accessioned2018-08-23T09:26:09Z
dc.date.available2018-08-23T09:26:09Z
dc.date.issued2014-07
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/10259/4877
dc.description.abstractTwo families of regioisomeric 1,4-benzodiazepines, 4-benzyl-3H-benzo[e][1,4]diazepin-5-ones and 4-benzoyl-4,5-dihydro-3H-benzo[e][1,4]diazepines, have been synthesized through a similar Ugi/reduction cyclization sequence. Their conformation and stability depend on the position of the tautomeric imine/enamine equilibrium present in the diazepine nucleus, which in turn depends on the relative position of the carbonyl group adjacent to the nitrogen at the 4-position in the benzodiazepine system. Moreover, the electrophilic center on the imine tautomer is essential for the antitumor activity of some benzodiazepines as a DNA binding position. The mechanism of tautomerization in the presence or absence of the oxo group has been studied computationally using DFT methods (B3LYP/6-31G** level).en
dc.description.sponsorshipMinisterio de Economía y Competitividad, Spain (project CTQ2012- 31611), from Ministerio de Ciencia e Innovación, Spain and Fondo de Desarrollo Regional (project MAT2011-22781), as well as from Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo (project ref. BU246A12-1 and BU327A11-2).en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofOrganic & Biomolecular Chemistry. 2014, V. 12, n. 27, p. 4905-4916en
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleExperimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepinesen
dc.typeinfo:eu-repo/semantics/article
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttps://doi.org/10.1039/C4OB00444B
dc.identifier.doi10.1039/C4OB00444B
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2012-31611
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN/MAT2011-22781
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU246A12-1
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU327A11-2
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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