2026-04-23T05:53:43Zhttps://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 b9e6524a-c9e8-44a9-9cf8-befd2d6cd56a 500 García Valverde, María 222 500 Peña Calleja, Pablo 426 500 0000-0001-9483-9808 Cordero Tejedor, Nicolás A. 128 500 Torroba Pérez, Tomás 554 500 González Ortega, Alfonso . 3eb69046-344a-48bd-bd00-44d54652512c 500 2018-08-23T09:26:09Z 2018-08-23T09:26:09Z 2014-07 1477-0520 http://hdl.handle.net/10259/4877 10.1039/C4OB00444B 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). application/pdf eng Royal Society of Chemistry 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 Química orgánica Chemistry, Organic Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess THUMBNAIL Pertejo-OBC_2014.pdf.jpg Pertejo-OBC_2014.pdf.jpg IM Thumbnail image/jpeg 3881 https://riubu.ubu.es/bitstream/10259/4877/4/Pertejo-OBC_2014.pdf.jpg 0629748d632b9ea8100461eeaae9bed3 MD5 4 ORIGINAL Pertejo-OBC_2014.pdf Pertejo-OBC_2014.pdf application/pdf 1785911 https://riubu.ubu.es/bitstream/10259/4877/1/Pertejo-OBC_2014.pdf ecf9a876634eec1cd22c132cd6660fc6 MD5 1 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/4877/2/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 2 TEXT Pertejo-OBC_2014.pdf.txt Pertejo-OBC_2014.pdf.txt Extracted text text/plain 55138 https://riubu.ubu.es/bitstream/10259/4877/3/Pertejo-OBC_2014.pdf.txt 5b6355e773ad4d1f8114119c7a9bc3db MD5 3 10259/4877 oai:riubu.ubu.es:10259/4877 2021-11-10 10:38:19.622 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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