2026-04-20T01:52:06Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/52412021-11-02T12:01:33Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

Pertejo Fernández, Pablo b9e6524a-c9e8-44a9-9cf8-befd2d6cd56a 500 Carreira Barral, Israel 703d8822-8907-4c5b-9bdd-773fda8112db 500 Peña Calleja, Pablo 426 500 0000-0001-9483-9808 Quesada Pato, Roberto 458 500 García Valverde, María 222 500 2020-03-11T11:23:12Z 2020-03-11T11:23:12Z 2020-01 0022-3263 http://hdl.handle.net/10259/5241 10.1021/acs.joc.9b02995 1520-6904 The synthesis of three novel families of pyrrolo[2,1-c][1,4]benzodiazepine-5-ones is described. The compounds were prepared according to a three-step sequence, involving an Ugi reaction, building of the pyrrolo nucleus, and reduction–cyclization to the corresponding diazepine. Depending on the amine employed in the synthesis of the Ugi adducts, different unsaturation degrees could be obtained in the pyrrolo ring (saturated or with endo or exo unsaturations), a key feature determining their biological activity, as it affects the affinity of the pyrrolobenzodiazepines toward DNA and thus their cytotoxicity. This synthetic methodology represents a significant improvement with respect to those described in the literature so far, as it uses inexpensive and commercially available starting materials without needing derivatization or the use of protecting groups. Consejería de Educación de la Junta de Castilla y León (project BU075G19) application/pdf eng American Chemical Society The Journal of Organic. 2020, V. 85, n. 4, p. 2291-2302 https://doi.org/10.1021/acs.joc.9b02995 info:eu-repo/grantAgreement/JCyL/BU075G19 Mixtures Inorganic carbon compounds Adducts Cyclization Chemical synthesis Química orgánica Chemistry, Organic Post-Ugi transformations for the access to pyrrolobenzodiazepine scaffolds with different degrees of unsaturation info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess The Journal of Organic Chemistry 85 4 2291 2302 ORIGINAL Pertejo-joc_2020.pdf Pertejo-joc_2020.pdf application/pdf 408102 https://riubu.ubu.es/bitstream/10259/5241/1/Pertejo-joc_2020.pdf 496ca97ac6435f10f5195f216034e4db MD5 1 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/5241/2/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 2 THUMBNAIL Pertejo-joc_2020.pdf.jpg Pertejo-joc_2020.pdf.jpg IM Thumbnail image/jpeg 3808 https://riubu.ubu.es/bitstream/10259/5241/3/Pertejo-joc_2020.pdf.jpg 0ac74b6049111388b8b1d10f26af24f1 MD5 3 TEXT Pertejo-joc_2020.pdf.txt Pertejo-joc_2020.pdf.txt Extracted text text/plain 84016 https://riubu.ubu.es/bitstream/10259/5241/4/Pertejo-joc_2020.pdf.txt 40bb3148444ea53639e46ab6b4c1d20c MD5 4 10259/5241 oai:riubu.ubu.es:10259/5241 2021-11-02 13:01:33.348 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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