New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole

Autores
Gutierrez, Carolina Guadalupe; Machuca, Laura Marcela; Acuña Ojeda, Maria Florencia; Alfaro, Esteban; Spagnolo, Lorena Cecilia; Murguia, Marcelo Cesar
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of new 3-[(amino)methyl]-1,3-benzothiazole-2-thione 4(a-l) were synthesized by Mannichreaction from formaldehyde, aliphatic or aromatic amines and 2-mercaptobenzothiazole. All synthesized compounds were in good agreement with elemental and spectral data (1H NMR and mass spectroscopy) and were evaluated for in vitro antifungal activity by agar well diffusion method. Fluconazole was included in the assays as a commercially available reference compound. Four fungal strains were used to perform the study: Cladosporium cladosporioides, Aspergillus niger ATCC 16404, Botrytis sp. and Rhizopus sp. Compounds 4a-c, 4e-g, 4i and 4l were found to be active against the four moulds mentioned, due to the presence of inhibitory halo. 4h was active in case of C. cladosporioides. Compounds 4d, 4j and 4k did not show inhibition against fungi used for the test. Fluconazole showed biological activity against Aspergillus niger ATCC 16404 and Botrytis sp. Therefore, 8 of the 12 synthesized substances would be considered as promising products to the treatment of fungal diseases.
Fil: Gutierrez, Carolina Guadalupe. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; Argentina
Fil: Machuca, Laura Marcela. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Acuña Ojeda, Maria Florencia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Alfaro, Esteban. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Spagnolo, Lorena Cecilia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Murguia, Marcelo Cesar. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
Materia
MANNICH
2-MERCAPTOBENZOTHIAZOLE
ANTIFUNGAL
AGAR WELL
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:11336/223794
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/223794
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-MercaptobenzothiazoleGutierrez, Carolina GuadalupeMachuca, Laura MarcelaAcuña Ojeda, Maria FlorenciaAlfaro, EstebanSpagnolo, Lorena CeciliaMurguia, Marcelo CesarMANNICH2-MERCAPTOBENZOTHIAZOLEANTIFUNGALAGAR WELLhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1A series of new 3-[(amino)methyl]-1,3-benzothiazole-2-thione 4(a-l) were synthesized by Mannichreaction from formaldehyde, aliphatic or aromatic amines and 2-mercaptobenzothiazole. All synthesized compounds were in good agreement with elemental and spectral data (1H NMR and mass spectroscopy) and were evaluated for in vitro antifungal activity by agar well diffusion method. Fluconazole was included in the assays as a commercially available reference compound. Four fungal strains were used to perform the study: Cladosporium cladosporioides, Aspergillus niger ATCC 16404, Botrytis sp. and Rhizopus sp. Compounds 4a-c, 4e-g, 4i and 4l were found to be active against the four moulds mentioned, due to the presence of inhibitory halo. 4h was active in case of C. cladosporioides. Compounds 4d, 4j and 4k did not show inhibition against fungi used for the test. Fluconazole showed biological activity against Aspergillus niger ATCC 16404 and Botrytis sp. Therefore, 8 of the 12 synthesized substances would be considered as promising products to the treatment of fungal diseases.Fil: Gutierrez, Carolina Guadalupe. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; ArgentinaFil: Machuca, Laura Marcela. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Acuña Ojeda, Maria Florencia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Alfaro, Esteban. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Spagnolo, Lorena Cecilia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Murguia, Marcelo Cesar. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; ArgentinaEM International2023-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/223794Gutierrez, Carolina Guadalupe; Machuca, Laura Marcela; Acuña Ojeda, Maria Florencia; Alfaro, Esteban; Spagnolo, Lorena Cecilia; et al.; New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole; EM International; Asian Journal of Microbiology, Biotechnology and Environmental Sciences; 25; 1; 4-2023; 1-80972-3005CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.envirobiotechjournals.com/article_abstract.php?aid=13620&iid=374&jid=1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:36:41Zoai:ri.conicet.gov.ar:11336/223794instacron: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 10:36:41.637CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
title New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
spellingShingle New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
Gutierrez, Carolina Guadalupe
MANNICH
2-MERCAPTOBENZOTHIAZOLE
ANTIFUNGAL
AGAR WELL
title_short New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
title_full New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
title_fullStr New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
title_full_unstemmed New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
title_sort New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole
dc.creator.none.fl_str_mv Gutierrez, Carolina Guadalupe
Machuca, Laura Marcela
Acuña Ojeda, Maria Florencia
Alfaro, Esteban
Spagnolo, Lorena Cecilia
Murguia, Marcelo Cesar
author Gutierrez, Carolina Guadalupe
author_facet Gutierrez, Carolina Guadalupe
Machuca, Laura Marcela
Acuña Ojeda, Maria Florencia
Alfaro, Esteban
Spagnolo, Lorena Cecilia
Murguia, Marcelo Cesar
author_role author
author2 Machuca, Laura Marcela
Acuña Ojeda, Maria Florencia
Alfaro, Esteban
Spagnolo, Lorena Cecilia
Murguia, Marcelo Cesar
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv MANNICH
2-MERCAPTOBENZOTHIAZOLE
ANTIFUNGAL
AGAR WELL
topic MANNICH
2-MERCAPTOBENZOTHIAZOLE
ANTIFUNGAL
AGAR WELL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of new 3-[(amino)methyl]-1,3-benzothiazole-2-thione 4(a-l) were synthesized by Mannichreaction from formaldehyde, aliphatic or aromatic amines and 2-mercaptobenzothiazole. All synthesized compounds were in good agreement with elemental and spectral data (1H NMR and mass spectroscopy) and were evaluated for in vitro antifungal activity by agar well diffusion method. Fluconazole was included in the assays as a commercially available reference compound. Four fungal strains were used to perform the study: Cladosporium cladosporioides, Aspergillus niger ATCC 16404, Botrytis sp. and Rhizopus sp. Compounds 4a-c, 4e-g, 4i and 4l were found to be active against the four moulds mentioned, due to the presence of inhibitory halo. 4h was active in case of C. cladosporioides. Compounds 4d, 4j and 4k did not show inhibition against fungi used for the test. Fluconazole showed biological activity against Aspergillus niger ATCC 16404 and Botrytis sp. Therefore, 8 of the 12 synthesized substances would be considered as promising products to the treatment of fungal diseases.
Fil: Gutierrez, Carolina Guadalupe. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; Argentina
Fil: Machuca, Laura Marcela. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Acuña Ojeda, Maria Florencia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Alfaro, Esteban. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Spagnolo, Lorena Cecilia. Universidad de la Cuenca del Plata. Secretaria de Politicas del Conocimiento. Instituto de Investigaciones Científicas (sede Goya); Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Murguia, Marcelo Cesar. Universidad Nacional del Litoral. Facultad de Bioquimica y Ciencias Biologicas. Laboratorio de Química Aplicada.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
description A series of new 3-[(amino)methyl]-1,3-benzothiazole-2-thione 4(a-l) were synthesized by Mannichreaction from formaldehyde, aliphatic or aromatic amines and 2-mercaptobenzothiazole. All synthesized compounds were in good agreement with elemental and spectral data (1H NMR and mass spectroscopy) and were evaluated for in vitro antifungal activity by agar well diffusion method. Fluconazole was included in the assays as a commercially available reference compound. Four fungal strains were used to perform the study: Cladosporium cladosporioides, Aspergillus niger ATCC 16404, Botrytis sp. and Rhizopus sp. Compounds 4a-c, 4e-g, 4i and 4l were found to be active against the four moulds mentioned, due to the presence of inhibitory halo. 4h was active in case of C. cladosporioides. Compounds 4d, 4j and 4k did not show inhibition against fungi used for the test. Fluconazole showed biological activity against Aspergillus niger ATCC 16404 and Botrytis sp. Therefore, 8 of the 12 synthesized substances would be considered as promising products to the treatment of fungal diseases.
publishDate 2023
dc.date.none.fl_str_mv 2023-04
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/11336/223794
Gutierrez, Carolina Guadalupe; Machuca, Laura Marcela; Acuña Ojeda, Maria Florencia; Alfaro, Esteban; Spagnolo, Lorena Cecilia; et al.; New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole; EM International; Asian Journal of Microbiology, Biotechnology and Environmental Sciences; 25; 1; 4-2023; 1-8
0972-3005
CONICET Digital
CONICET
url http://hdl.handle.net/11336/223794
identifier_str_mv Gutierrez, Carolina Guadalupe; Machuca, Laura Marcela; Acuña Ojeda, Maria Florencia; Alfaro, Esteban; Spagnolo, Lorena Cecilia; et al.; New Antifungal Agents: Synthesis, Characterization and Biological Activity of Some Mannich Bases Derived from 2-Mercaptobenzothiazole; EM International; Asian Journal of Microbiology, Biotechnology and Environmental Sciences; 25; 1; 4-2023; 1-8
0972-3005
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.envirobiotechjournals.com/article_abstract.php?aid=13620&iid=374&jid=1
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
application/pdf
dc.publisher.none.fl_str_mv EM International
publisher.none.fl_str_mv EM International
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 13.070432

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