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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/4877

    Título
    Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines
    Autor
    Pertejo Fernández, Pablo
    García Valverde, MaríaUBU authority Orcid
    Peña Calleja, PabloUBU authority Orcid
    Cordero Tejedor, Nicolás A.UBU authority Orcid
    Torroba Pérez, TomásUBU authority Orcid
    González Ortega, Alfonso .
    Publicado en
    Organic & Biomolecular Chemistry. 2014, V. 12, n. 27, p. 4905-4916
    Editorial
    Royal Society of Chemistry
    Fecha de publicación
    2014-07
    ISSN
    1477-0520
    DOI
    10.1039/C4OB00444B
    Abstract
    Two 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).
    Materia
    Química orgánica
    Chemistry, Organic
    URI
    http://hdl.handle.net/10259/4877
    Versión del editor
    https://doi.org/10.1039/C4OB00444B
    Collections
    • Artículos BIOORG
    • Artículos SUPRABUR
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