RT info:eu-repo/semantics/article
T1 Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines
A1 Pertejo Fernández, Pablo
A1 García Valverde, María
A1 Peña Calleja, Pablo
A1 Cordero Tejedor, Nicolás A.
A1 Torroba Pérez, Tomás
A1 González Ortega, Alfonso .
K1 Química orgánica
K1 Chemistry, Organic
AB 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).
PB Royal Society of Chemistry
SN 1477-0520
YR 2014
FD 2014-07
LK http://hdl.handle.net/10259/4877
UL http://hdl.handle.net/10259/4877
LA eng
NO Ministeriode Economía y Competitividad, Spain (project CTQ2012-31611), from Ministerio de Ciencia e Innovación, Spain andFondo de Desarrollo Regional (project MAT2011-22781), aswell as from Junta de Castilla y León, Consejería de Educacióny Cultura y Fondo Social Europeo (project ref. BU246A12-1 andBU327A11-2).
DS Repositorio Institucional de la Universidad de Burgos
RD 11-dic-2024