2026-05-07T12:57:17Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/48772021-11-10T09:38:19Zcom_10259_3924com_10259_5086com_10259_2604com_10259_4354col_10259_3925col_10259_4355

Pertejo Fernández, Pablo García Valverde, María Peña Calleja, Pablo Cordero Tejedor, Nicolás A. Torroba Pérez, Tomás González Ortega, Alfonso . 2014-07 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). application/pdf http://hdl.handle.net/10259/4877 eng Royal Society of Chemistry Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines info:eu-repo/semantics/article TEXT RIUBU. Repositorio Institucional de la Universidad de Burgos Hispana