Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5...

Descripción completa

Detalles Bibliográficos
Autores principales: Hemming, Karl, Chambers, Christopher S., Jamshaid, Faisal, O’Gorman, Paul A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271382/
https://www.ncbi.nlm.nih.gov/pubmed/25329868
http://dx.doi.org/10.3390/molecules191016737
_version_ 1783376915976945664
author Hemming, Karl
Chambers, Christopher S.
Jamshaid, Faisal
O’Gorman, Paul A.
author_facet Hemming, Karl
Chambers, Christopher S.
Jamshaid, Faisal
O’Gorman, Paul A.
author_sort Hemming, Karl
collection PubMed
description The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.
format Online
Article
Text
id pubmed-6271382
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62713822018-12-27 Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines Hemming, Karl Chambers, Christopher S. Jamshaid, Faisal O’Gorman, Paul A. Molecules Article The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics. MDPI 2014-10-17 /pmc/articles/PMC6271382/ /pubmed/25329868 http://dx.doi.org/10.3390/molecules191016737 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Hemming, Karl
Chambers, Christopher S.
Jamshaid, Faisal
O’Gorman, Paul A.
Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title_full Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title_fullStr Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title_full_unstemmed Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title_short Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
title_sort intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271382/
https://www.ncbi.nlm.nih.gov/pubmed/25329868
http://dx.doi.org/10.3390/molecules191016737
work_keys_str_mv AT hemmingkarl intramolecularazidetoalkenecycloadditionsfortheconstructionofpyrrolobenzodiazepinesandazetidinobenzodiazepines
AT chamberschristophers intramolecularazidetoalkenecycloadditionsfortheconstructionofpyrrolobenzodiazepinesandazetidinobenzodiazepines
AT jamshaidfaisal intramolecularazidetoalkenecycloadditionsfortheconstructionofpyrrolobenzodiazepinesandazetidinobenzodiazepines
AT ogormanpaula intramolecularazidetoalkenecycloadditionsfortheconstructionofpyrrolobenzodiazepinesandazetidinobenzodiazepines

Ejemplares similares