2026-05-07T12:58:25Zhttps://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

00925njm 22002777a 4500 dc Pertejo Fernández, Pablo author García Valverde, María author Peña Calleja, Pablo author Cordero Tejedor, Nicolás A. author Torroba Pérez, Tomás author González Ortega, Alfonso . author 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). 1477-0520 http://hdl.handle.net/10259/4877 10.1039/C4OB00444B Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines