Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs

Autores
Barazarte, Arthur; Camacho, José; Domínguez, José; Lobo, Gricela; Gamboa, Neira; Rodrigues, Juan; Capparelli, Mario V.; Álvarez Larena, Ángel; Andujar, Sebastian Antonio; Enriz, Ricardo Daniel; Charris, Jaime
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response.
Fil: Barazarte, Arthur. Universidad Central de Venezuela; Venezuela
Fil: Camacho, José. Universidad Central de Venezuela; Venezuela
Fil: Domínguez, José. Universidad Central de Venezuela; Venezuela
Fil: Lobo, Gricela. Universidad Central de Venezuela; Venezuela
Fil: Gamboa, Neira. Universidad Central de Venezuela; Venezuela
Fil: Rodrigues, Juan. Universidad Central de Venezuela; Venezuela
Fil: Capparelli, Mario V.. Universidad Central de Venezuela; Venezuela
Fil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; España
Fil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Charris, Jaime. Universidad Central de Venezuela; Venezuela
Materia
1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
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:11336/129237
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/129237
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogsBarazarte, ArthurCamacho, JoséDomínguez, JoséLobo, GricelaGamboa, NeiraRodrigues, JuanCapparelli, Mario V.Álvarez Larena, ÁngelAndujar, Sebastian AntonioEnriz, Ricardo DanielCharris, Jaime1,4-BENZOTHIAZINESANTIMALARIALCYCLIZATIONSAR STUDYTHIENOhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response.Fil: Barazarte, Arthur. Universidad Central de Venezuela; VenezuelaFil: Camacho, José. Universidad Central de Venezuela; VenezuelaFil: Domínguez, José. Universidad Central de Venezuela; VenezuelaFil: Lobo, Gricela. Universidad Central de Venezuela; VenezuelaFil: Gamboa, Neira. Universidad Central de Venezuela; VenezuelaFil: Rodrigues, Juan. Universidad Central de Venezuela; VenezuelaFil: Capparelli, Mario V.. Universidad Central de Venezuela; VenezuelaFil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; EspañaFil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Charris, Jaime. Universidad Central de Venezuela; VenezuelaPergamon-Elsevier Science Ltd2008-04info: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/11336/129237Barazarte, Arthur; Camacho, José; Domínguez, José; Lobo, Gricela; Gamboa, Neira; et al.; Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 7; 4-2008; 3661-36740968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S096808960800120Xinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2008.02.011info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:13:42Zoai:ri.conicet.gov.ar:11336/129237instacron: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:34982025-09-29 10:13:42.555CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
title Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
spellingShingle Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
Barazarte, Arthur
1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
title_short Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
title_full Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
title_fullStr Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
title_full_unstemmed Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
title_sort Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
dc.creator.none.fl_str_mv Barazarte, Arthur
Camacho, José
Domínguez, José
Lobo, Gricela
Gamboa, Neira
Rodrigues, Juan
Capparelli, Mario V.
Álvarez Larena, Ángel
Andujar, Sebastian Antonio
Enriz, Ricardo Daniel
Charris, Jaime
author Barazarte, Arthur
author_facet Barazarte, Arthur
Camacho, José
Domínguez, José
Lobo, Gricela
Gamboa, Neira
Rodrigues, Juan
Capparelli, Mario V.
Álvarez Larena, Ángel
Andujar, Sebastian Antonio
Enriz, Ricardo Daniel
Charris, Jaime
author_role author
author2 Camacho, José
Domínguez, José
Lobo, Gricela
Gamboa, Neira
Rodrigues, Juan
Capparelli, Mario V.
Álvarez Larena, Ángel
Andujar, Sebastian Antonio
Enriz, Ricardo Daniel
Charris, Jaime
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
topic 1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response.
Fil: Barazarte, Arthur. Universidad Central de Venezuela; Venezuela
Fil: Camacho, José. Universidad Central de Venezuela; Venezuela
Fil: Domínguez, José. Universidad Central de Venezuela; Venezuela
Fil: Lobo, Gricela. Universidad Central de Venezuela; Venezuela
Fil: Gamboa, Neira. Universidad Central de Venezuela; Venezuela
Fil: Rodrigues, Juan. Universidad Central de Venezuela; Venezuela
Fil: Capparelli, Mario V.. Universidad Central de Venezuela; Venezuela
Fil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; España
Fil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Charris, Jaime. Universidad Central de Venezuela; Venezuela
description An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response.
publishDate 2008
dc.date.none.fl_str_mv 2008-04
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/11336/129237
Barazarte, Arthur; Camacho, José; Domínguez, José; Lobo, Gricela; Gamboa, Neira; et al.; Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 7; 4-2008; 3661-3674
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/129237
identifier_str_mv Barazarte, Arthur; Camacho, José; Domínguez, José; Lobo, Gricela; Gamboa, Neira; et al.; Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 16; 7; 4-2008; 3661-3674
0968-0896
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S096808960800120X
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2008.02.011
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
_version_ 1844614057349349376
score 13.070432

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