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

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 th...

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Detalles Bibliográficos
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
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2008
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/129237
Acceso en línea:http://hdl.handle.net/11336/129237
Access Level:acceso abierto
Palabra clave:1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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network_acronym_str AR
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repository_id_str
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 Técnicas2024-05-08T14:03:45Zoai: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:34982024-05-08 14:03:45.59CONICET 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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic 1,4-BENZOTHIAZINES
ANTIMALARIAL
CYCLIZATION
SAR STUDY
THIENO
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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_ 1799195795959840768
score 15,811543

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