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

Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines Pertejo Fernández, Pablo García Valverde, María Peña Calleja, Pablo Cordero Tejedor, Nicolás A. Torroba Pérez, Tomás González Ortega, Alfonso . Química orgánica Chemistry, Organic 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). Ministerio 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). 2018-08-23T09:26:09Z 2018-08-23T09:26:09Z 2014-07 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1477-0520 http://hdl.handle.net/10259/4877 10.1039/C4OB00444B eng Organic & Biomolecular Chemistry. 2014, V. 12, n. 27, p. 4905-4916 https://doi.org/10.1039/C4OB00444B info:eu-repo/grantAgreement/MINECO/CTQ2012-31611 info:eu-repo/grantAgreement/MICINN/MAT2011-22781 info:eu-repo/grantAgreement/JCyL/BU246A12-1 info:eu-repo/grantAgreement/JCyL/BU327A11-2 info:eu-repo/semantics/openAccess application/pdf Royal Society of Chemistry