Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines

Autores
Pagliero, Romina Julieta; Lusvarghi, Sabrina; Pierini, Adriana Beatriz; Brun, Reto; Mazzieri, Maria Rosa
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the 1H NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H⋯O{double bond, long}S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference.
Fil: Pagliero, Romina Julieta. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Lusvarghi, Sabrina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Brun, Reto. Parasite Chemotherapy, Swiss Tropical Institute; Suiza
Fil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Materia
Antiparasitic Compounds
Benzenesulfonyl Derivatives
Tetrahydroquinolines
Synthesis And Biological Activity
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:11336/67512
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolinesPagliero, Romina JulietaLusvarghi, SabrinaPierini, Adriana BeatrizBrun, RetoMazzieri, Maria RosaAntiparasitic CompoundsBenzenesulfonyl DerivativesTetrahydroquinolinesSynthesis And Biological Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the 1H NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H⋯O{double bond, long}S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference.Fil: Pagliero, Romina Julieta. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Lusvarghi, Sabrina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaFil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Brun, Reto. Parasite Chemotherapy, Swiss Tropical Institute; SuizaFil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; ArgentinaPergamon-Elsevier Science Ltd2010-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/67512Pagliero, Romina Julieta; Lusvarghi, Sabrina; Pierini, Adriana Beatriz; Brun, Reto; Mazzieri, Maria Rosa; Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 18; 1; 1-2010; 142-1500968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0968089609010189info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2009.11.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:35:34Zoai:ri.conicet.gov.ar:11336/67512instacron: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:34982025-10-15 14:35:34.767CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
title Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
spellingShingle Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
Pagliero, Romina Julieta
Antiparasitic Compounds
Benzenesulfonyl Derivatives
Tetrahydroquinolines
Synthesis And Biological Activity
title_short Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
title_full Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
title_fullStr Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
title_full_unstemmed Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
title_sort Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines
dc.creator.none.fl_str_mv Pagliero, Romina Julieta
Lusvarghi, Sabrina
Pierini, Adriana Beatriz
Brun, Reto
Mazzieri, Maria Rosa
author Pagliero, Romina Julieta
author_facet Pagliero, Romina Julieta
Lusvarghi, Sabrina
Pierini, Adriana Beatriz
Brun, Reto
Mazzieri, Maria Rosa
author_role author
author2 Lusvarghi, Sabrina
Pierini, Adriana Beatriz
Brun, Reto
Mazzieri, Maria Rosa
author2_role author
author
author
author
dc.subject.none.fl_str_mv Antiparasitic Compounds
Benzenesulfonyl Derivatives
Tetrahydroquinolines
Synthesis And Biological Activity
topic Antiparasitic Compounds
Benzenesulfonyl Derivatives
Tetrahydroquinolines
Synthesis And Biological Activity
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 and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the 1H NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H⋯O{double bond, long}S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference.
Fil: Pagliero, Romina Julieta. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Lusvarghi, Sabrina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Brun, Reto. Parasite Chemotherapy, Swiss Tropical Institute; Suiza
Fil: Mazzieri, Maria Rosa. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
description The synthesis and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the 1H NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H⋯O{double bond, long}S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference.
publishDate 2010
dc.date.none.fl_str_mv 2010-01
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/11336/67512
Pagliero, Romina Julieta; Lusvarghi, Sabrina; Pierini, Adriana Beatriz; Brun, Reto; Mazzieri, Maria Rosa; Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 18; 1; 1-2010; 142-150
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/67512
identifier_str_mv Pagliero, Romina Julieta; Lusvarghi, Sabrina; Pierini, Adriana Beatriz; Brun, Reto; Mazzieri, Maria Rosa; Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 18; 1; 1-2010; 142-150
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/pii/S0968089609010189
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2009.11.010
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
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_ 1846082816395182080
score 13.22299

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