Author | Evangelista, Tereza Cristina Santos | |
Author | Delarmelina, Maicon | |
Author | Addla, Dinesh | |
Author | Allão, Rafael A. | |
Author | Kaiser, Carlos Roland | |
Author | Carneiro, José Walkimar de M. | |
Author | Silva Jr., Floriano Paes | |
Author | Ferreira, Sabrina Baptista | |
Access date | 2021-07-16T14:25:11Z | |
Available date | 2021-07-16T14:25:11Z | |
Document date | 2021 | |
Citation | EVANGELISTA, Tereza Cristina Santos et al. Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways. Tetrahedron Letters, v. 68, 152937, 5 p, Feb. 2021. | pt_BR |
ISSN | 0040-4039 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/48258 | |
Language | eng | pt_BR |
Publisher | Elsevier | pt_BR |
Rights | restricted access | |
Subject in Portuguese | Azida Sódica | pt_BR |
Subject in Portuguese | Demência Frontotemporal | pt_BR |
Subject in Portuguese | Pyrrolobenzodiazepines | pt_BR |
Subject in Portuguese | Reações de substituição nucleofílica | pt_BR |
Subject in Portuguese | Diastereoisômeros | pt_BR |
Subject in Portuguese | Temperatura | pt_BR |
Title | Influence of temperature for the azide displacement in benzodiazepine derivatives: Experimental and DFT study of competing SN1, SN2 and double SN2 reaction pathways | pt_BR |
Type | Article | |
DOI | 10.1016/j.tetlet.2021.152937 | |
Abstract | Molecules carrying the azido functionality are widely used as intermediates in medicinal chemistry.
Pyrrolobenzodiazepines are molecules with a broad range of interesting pharmacological properties.
Due to the wide importance of azido-PBD as a key intermediate in many synthetic pathways, in this work
we have investigated the effect of a variety of experimental parameters on the mechanism of nucleophilic
substitution reaction for introducing an azide group into the PBD scaffold. This study was carried out by
combined experimental and DFT approaches, showing that SN2 and double SN2 pathways are possible
and highly dependent on the reaction temperature. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Síntese Orgânica e Prospecção Biológica. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal Fluminense. Instituto de Química. Niterói, RJ, Brasil / Cardiff University. School of Chemistry. Cardiff, United Kingdom. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Síntese Orgânica e Prospecção Biológica. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química.. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Síntese Orgânica e Prospecção Biológica. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal Fluminense. Instituto de Química. Niterói, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Bioquímica Experimental e Computacional de Fármacos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Laboratório de Síntese Orgânica e Prospecção Biológica. Rio de Janeiro, RJ, Brasil. | pt_BR |
Subject | Azide | pt_BR |
Subject | DFT | pt_BR |
Subject | Pyrrolobenzodiazepines | pt_BR |
Subject | Nucleophilic substitution reactions | pt_BR |
Subject | Diastereoisomers | pt_BR |
Subject | Temperature | pt_BR |
DeCS | Azida Sódica | pt_BR |
DeCS | Demência Frontotemporal | pt_BR |
DeCS | Agnosia | pt_BR |