Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics

Autores
Ding, Derong; Boudreau, Marc A.; Leemans, Erika J.; Spink, Edward; Yamaguchi, Takao; Testero, Sebastian Andres; O'Daniel, Peter I.; Lastochkin, Elena; Chang, Mayland; Mobashery, Shahriar
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We have recently disclosed the discovery of the class of 1,2,4-oxadiazole antibiotics, which emerged from in silico docking and scoring efforts. This class of antibacterials exhibits Gram-positive activity, particularly against Staphylococcus aureus. We define the structure–activity relationship (SAR) of this class of antibiotics with the synthesis and evaluation of a series of 59 derivatives with variations in the C ring or C and D rings. A total of 17 compounds showed activity against S. aureus. Four derivatives were evaluated against a panel of 16 Gram-positive strains, inclusive of several methicillin-resistant S. aureus strains. These compounds are broadly active against Gram-positive bacteria.
Fil: Ding, Derong. University Of Notre Dame-indiana; Estados Unidos
Fil: Boudreau, Marc A.. University Of Notre Dame-indiana; Estados Unidos
Fil: Leemans, Erika J.. University Of Notre Dame-indiana; Estados Unidos
Fil: Spink, Edward. University Of Notre Dame-indiana; Estados Unidos
Fil: Yamaguchi, Takao. University Of Notre Dame-indiana; Estados Unidos
Fil: Testero, Sebastian Andres. University Of Notre Dame-indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: O'Daniel, Peter I.. University Of Notre Dame-indiana; Estados Unidos
Fil: Lastochkin, Elena. University Of Notre Dame-indiana; Estados Unidos
Fil: Chang, Mayland. University Of Notre Dame-indiana; Estados Unidos
Fil: Mobashery, Shahriar. University Of Notre Dame-indiana; Estados Unidos
Materia
1,2,4-Oxadiazoles
Structureactivity Relationship
Antibiotics
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6004
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6004
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole AntibioticsDing, DerongBoudreau, Marc A.Leemans, Erika J.Spink, EdwardYamaguchi, TakaoTestero, Sebastian AndresO'Daniel, Peter I.Lastochkin, ElenaChang, MaylandMobashery, Shahriar1,2,4-OxadiazolesStructureactivity RelationshipAntibioticshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have recently disclosed the discovery of the class of 1,2,4-oxadiazole antibiotics, which emerged from in silico docking and scoring efforts. This class of antibacterials exhibits Gram-positive activity, particularly against Staphylococcus aureus. We define the structure–activity relationship (SAR) of this class of antibiotics with the synthesis and evaluation of a series of 59 derivatives with variations in the C ring or C and D rings. A total of 17 compounds showed activity against S. aureus. Four derivatives were evaluated against a panel of 16 Gram-positive strains, inclusive of several methicillin-resistant S. aureus strains. These compounds are broadly active against Gram-positive bacteria.Fil: Ding, Derong. University Of Notre Dame-indiana; Estados UnidosFil: Boudreau, Marc A.. University Of Notre Dame-indiana; Estados UnidosFil: Leemans, Erika J.. University Of Notre Dame-indiana; Estados UnidosFil: Spink, Edward. University Of Notre Dame-indiana; Estados UnidosFil: Yamaguchi, Takao. University Of Notre Dame-indiana; Estados UnidosFil: Testero, Sebastian Andres. University Of Notre Dame-indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: O'Daniel, Peter I.. University Of Notre Dame-indiana; Estados UnidosFil: Lastochkin, Elena. University Of Notre Dame-indiana; Estados UnidosFil: Chang, Mayland. University Of Notre Dame-indiana; Estados UnidosFil: Mobashery, Shahriar. University Of Notre Dame-indiana; Estados UnidosElsevier2015-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6004Ding, Derong; Boudreau, Marc A.; Leemans, Erika J.; Spink, Edward; Yamaguchi, Takao; et al.; Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 21; 6-2015; 4854-48570960-894Xenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X1500637Xinfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2015.06.044info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:11:10Zoai:ri.conicet.gov.ar:11336/6004instacron: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:34982025-10-22 12:11:11.131CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
title Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
spellingShingle Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
Ding, Derong
1,2,4-Oxadiazoles
Structureactivity Relationship
Antibiotics
title_short Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
title_full Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
title_fullStr Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
title_full_unstemmed Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
title_sort Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics
dc.creator.none.fl_str_mv Ding, Derong
Boudreau, Marc A.
Leemans, Erika J.
Spink, Edward
Yamaguchi, Takao
Testero, Sebastian Andres
O'Daniel, Peter I.
Lastochkin, Elena
Chang, Mayland
Mobashery, Shahriar
author Ding, Derong
author_facet Ding, Derong
Boudreau, Marc A.
Leemans, Erika J.
Spink, Edward
Yamaguchi, Takao
Testero, Sebastian Andres
O'Daniel, Peter I.
Lastochkin, Elena
Chang, Mayland
Mobashery, Shahriar
author_role author
author2 Boudreau, Marc A.
Leemans, Erika J.
Spink, Edward
Yamaguchi, Takao
Testero, Sebastian Andres
O'Daniel, Peter I.
Lastochkin, Elena
Chang, Mayland
Mobashery, Shahriar
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 1,2,4-Oxadiazoles
Structureactivity Relationship
Antibiotics
topic 1,2,4-Oxadiazoles
Structureactivity Relationship
Antibiotics
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We have recently disclosed the discovery of the class of 1,2,4-oxadiazole antibiotics, which emerged from in silico docking and scoring efforts. This class of antibacterials exhibits Gram-positive activity, particularly against Staphylococcus aureus. We define the structure–activity relationship (SAR) of this class of antibiotics with the synthesis and evaluation of a series of 59 derivatives with variations in the C ring or C and D rings. A total of 17 compounds showed activity against S. aureus. Four derivatives were evaluated against a panel of 16 Gram-positive strains, inclusive of several methicillin-resistant S. aureus strains. These compounds are broadly active against Gram-positive bacteria.
Fil: Ding, Derong. University Of Notre Dame-indiana; Estados Unidos
Fil: Boudreau, Marc A.. University Of Notre Dame-indiana; Estados Unidos
Fil: Leemans, Erika J.. University Of Notre Dame-indiana; Estados Unidos
Fil: Spink, Edward. University Of Notre Dame-indiana; Estados Unidos
Fil: Yamaguchi, Takao. University Of Notre Dame-indiana; Estados Unidos
Fil: Testero, Sebastian Andres. University Of Notre Dame-indiana; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: O'Daniel, Peter I.. University Of Notre Dame-indiana; Estados Unidos
Fil: Lastochkin, Elena. University Of Notre Dame-indiana; Estados Unidos
Fil: Chang, Mayland. University Of Notre Dame-indiana; Estados Unidos
Fil: Mobashery, Shahriar. University Of Notre Dame-indiana; Estados Unidos
description We have recently disclosed the discovery of the class of 1,2,4-oxadiazole antibiotics, which emerged from in silico docking and scoring efforts. This class of antibacterials exhibits Gram-positive activity, particularly against Staphylococcus aureus. We define the structure–activity relationship (SAR) of this class of antibiotics with the synthesis and evaluation of a series of 59 derivatives with variations in the C ring or C and D rings. A total of 17 compounds showed activity against S. aureus. Four derivatives were evaluated against a panel of 16 Gram-positive strains, inclusive of several methicillin-resistant S. aureus strains. These compounds are broadly active against Gram-positive bacteria.
publishDate 2015
dc.date.none.fl_str_mv 2015-06
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/11336/6004
Ding, Derong; Boudreau, Marc A.; Leemans, Erika J.; Spink, Edward; Yamaguchi, Takao; et al.; Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 21; 6-2015; 4854-4857
0960-894X
url http://hdl.handle.net/11336/6004
identifier_str_mv Ding, Derong; Boudreau, Marc A.; Leemans, Erika J.; Spink, Edward; Yamaguchi, Takao; et al.; Exploration of the Structure-Activity Relationship of 1,2,4-Oxadiazole Antibiotics; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 21; 6-2015; 4854-4857
0960-894X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X1500637X
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2015.06.044
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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
_version_ 1846782502207750144
score 12.982451

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