Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors

Autores
Saiz, Cecilia; Villamil, Valentina; Gonzalez, Mariano Martin; Rossi, María Agustina; Martínez, Lorena; Suescun, Leopoldo; Vila, Alejandro Jose; Mahler, Graciela
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithioazabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 μM.
Fil: Saiz, Cecilia. Universidad de la República; Uruguay
Fil: Villamil, Valentina. Universidad de la República; Uruguay
Fil: Gonzalez, Mariano Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Rossi, María Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Martínez, Lorena. Universidad de la República; Uruguay
Fil: Suescun, Leopoldo. Universidad de la República; Uruguay
Fil: Vila, Alejandro Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Mahler, Graciela. Universidad de la República; Uruguay
Materia
Synthesis
Oxazolidinylthiazolidines Bicycles
Inhibitors
Ndm-1
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/50288
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50288
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitorsSaiz, CeciliaVillamil, ValentinaGonzalez, Mariano MartinRossi, María AgustinaMartínez, LorenaSuescun, LeopoldoVila, Alejandro JoseMahler, GracielaSynthesisOxazolidinylthiazolidines BicyclesInhibitorsNdm-1https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithioazabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 μM.Fil: Saiz, Cecilia. Universidad de la República; UruguayFil: Villamil, Valentina. Universidad de la República; UruguayFil: Gonzalez, Mariano Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Rossi, María Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Martínez, Lorena. Universidad de la República; UruguayFil: Suescun, Leopoldo. Universidad de la República; UruguayFil: Vila, Alejandro Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; ArgentinaFil: Mahler, Graciela. Universidad de la República; UruguayPergamon-Elsevier Science Ltd2017-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/50288Saiz, Cecilia; Villamil, Valentina; Gonzalez, Mariano Martin; Rossi, María Agustina; Martínez, Lorena; et al.; Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 1; 1-2017; 110-1170957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2016.11.002info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0957416616302774info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5451161/info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:13:24Zoai:ri.conicet.gov.ar:11336/50288instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:13:25.073CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
title Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
spellingShingle Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
Saiz, Cecilia
Synthesis
Oxazolidinylthiazolidines Bicycles
Inhibitors
Ndm-1
title_short Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
title_full Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
title_fullStr Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
title_full_unstemmed Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
title_sort Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors
dc.creator.none.fl_str_mv Saiz, Cecilia
Villamil, Valentina
Gonzalez, Mariano Martin
Rossi, María Agustina
Martínez, Lorena
Suescun, Leopoldo
Vila, Alejandro Jose
Mahler, Graciela
author Saiz, Cecilia
author_facet Saiz, Cecilia
Villamil, Valentina
Gonzalez, Mariano Martin
Rossi, María Agustina
Martínez, Lorena
Suescun, Leopoldo
Vila, Alejandro Jose
Mahler, Graciela
author_role author
author2 Villamil, Valentina
Gonzalez, Mariano Martin
Rossi, María Agustina
Martínez, Lorena
Suescun, Leopoldo
Vila, Alejandro Jose
Mahler, Graciela
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Synthesis
Oxazolidinylthiazolidines Bicycles
Inhibitors
Ndm-1
topic Synthesis
Oxazolidinylthiazolidines Bicycles
Inhibitors
Ndm-1
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithioazabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 μM.
Fil: Saiz, Cecilia. Universidad de la República; Uruguay
Fil: Villamil, Valentina. Universidad de la República; Uruguay
Fil: Gonzalez, Mariano Martin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Rossi, María Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Martínez, Lorena. Universidad de la República; Uruguay
Fil: Suescun, Leopoldo. Universidad de la República; Uruguay
Fil: Vila, Alejandro Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Biología Molecular y Celular de Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Biología Molecular y Celular de Rosario; Argentina
Fil: Mahler, Graciela. Universidad de la República; Uruguay
description The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithioazabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 μM.
publishDate 2017
dc.date.none.fl_str_mv 2017-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/50288
Saiz, Cecilia; Villamil, Valentina; Gonzalez, Mariano Martin; Rossi, María Agustina; Martínez, Lorena; et al.; Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 1; 1-2017; 110-117
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50288
identifier_str_mv Saiz, Cecilia; Villamil, Valentina; Gonzalez, Mariano Martin; Rossi, María Agustina; Martínez, Lorena; et al.; Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 1; 1-2017; 110-117
0957-4166
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2016.11.002
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0957416616302774
info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5451161/
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.993085

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