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dc.contributor.authorPertejo Fernández, Pablo
dc.contributor.authorCarreira Barral, Israel
dc.contributor.authorPeña Calleja, Pablo 
dc.contributor.authorQuesada Pato, Roberto 
dc.contributor.authorGarcía Valverde, María 
dc.date.accessioned2020-03-11T11:23:12Z
dc.date.available2020-03-11T11:23:12Z
dc.date.issued2020-01
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10259/5241
dc.description.abstractThe 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.en
dc.description.sponsorshipConsejería de Educación de la Junta de Castilla y León (project BU075G19)es
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherAmerican Chemical Societyes
dc.relation.ispartofThe Journal of Organic. 2020, V. 85, n. 4, p. 2291-2302es
dc.subjectMixturesen
dc.subjectInorganic carbon compoundsen
dc.subjectAdductsen
dc.subjectCyclizationen
dc.subjectChemical synthesisen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titlePost-Ugi transformations for the access to pyrrolobenzodiazepine scaffolds with different degrees of unsaturationen
dc.typeinfo:eu-repo/semantics/article
dc.rights.accessRightsinfo:eu-repo/semantics/embargoedAccess
dc.relation.publisherversionhttps://doi.org/10.1021/acs.joc.9b02995
dc.identifier.doi10.1021/acs.joc.9b02995
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU075G19
dc.identifier.essn1520-6904
dc.journal.titleThe Journal of Organic Chemistryes
dc.volume.number85es
dc.issue.number4es
dc.page.initial2291es
dc.page.final2302es
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersion


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