Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars
Resumen:
A series of L-lyxo and L-xylo- pentofuranose-mimetic iminosugars and derivatives were efficiently synthesized in a stereoselective manner, through a concise strategy which involves an organocatalyzed Mannich reaction of an imine and a protected dioxanone as key step, using D-proline as catalyst. A preliminary evaluation of their activity as potential anti-trypanosomal agents was studied. One of the synthesized compounds showed an interesting activity against bloodstream Trypanosoma brucei brucei (EC,)=3.8 + 1.0 1M).
| 2022 | |
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CARBOHIDRATOS INMINOAZUCAR TRYPANOSOMA BRUCEI REACCION DE MANNICH ORGANOCATALISIS |
|
| Inglés | |
| Universidad de la República | |
| COLIBRI | |
| https://hdl.handle.net/20.500.12008/36737 | |
| Acceso abierto | |
| Licencia Creative Commons Atribución - No Comercial - Sin Derivadas (CC - By-NC-ND 4.0) |
| _version_ | 1877554836599209984 |
|---|---|
| author | Mesa, Juan M. |
| author2 | Comini, Marcelo A. Dibello, Estefanía Gamenara, Daniela |
| author2_role | author author author |
| author_facet | Mesa, Juan M. Comini, Marcelo A. Dibello, Estefanía Gamenara, Daniela |
| author_role | author |
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| collection | COLIBRI |
| dc.contributor.filiacion.none.fl_str_mv | Mesa Juan M. Universidad de la República (Uruguay). Facultad de Química. Departamento de Química Orgánica Comini Marcelo A. Instituto Pasteur (Uruguay). Grupo Biología Redox de Tripanosomátidos Dibello Estefanía. Universidad de la República (Uruguay). Facultad de Química. Departamento de Química Orgánica ; Instituto Pasteur (Uruguay). Grupo Biología Redox de Tripanosomátidos Gamenara Daniela |
| dc.creator.none.fl_str_mv | Mesa, Juan M. Comini, Marcelo A. Dibello, Estefanía Gamenara, Daniela |
| dc.date.accessioned.none.fl_str_mv | 2023-04-19T13:42:01Z |
| dc.date.available.none.fl_str_mv | 2023-04-19T13:42:01Z |
| dc.date.issued.none.fl_str_mv | 2022 |
| dc.description.abstract.none.fl_txt_mv | A series of L-lyxo and L-xylo- pentofuranose-mimetic iminosugars and derivatives were efficiently synthesized in a stereoselective manner, through a concise strategy which involves an organocatalyzed Mannich reaction of an imine and a protected dioxanone as key step, using D-proline as catalyst. A preliminary evaluation of their activity as potential anti-trypanosomal agents was studied. One of the synthesized compounds showed an interesting activity against bloodstream Trypanosoma brucei brucei (EC,)=3.8 + 1.0 1M). |
| dc.description.es.fl_txt_mv | Versión aceptada (Postprint) |
| dc.format.extent.es.fl_str_mv | 7 p. |
| dc.format.mimetype.es.fl_str_mv | application/pdf |
| dc.identifier.citation.es.fl_str_mv | Mesa, J, Comini, M, Dibello, E y Gamenara, D. "Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars". European Journal of Organic Chemistry. [en línea] 2022 v.34, 2022. -- e202200636 .. 7 p.. |
| dc.identifier.doi.none.fl_str_mv | 10.1002/ejoc.202200636 |
| dc.identifier.uri.none.fl_str_mv | https://hdl.handle.net/20.500.12008/36737 |
| dc.language.iso.none.fl_str_mv | en eng |
| dc.publisher.es.fl_str_mv | Wiley |
| dc.relation.none.fl_str_mv | European Journal of Organic Chemistry, v.34, 2022. -- e202200636 |
| dc.rights.license.none.fl_str_mv | Licencia Creative Commons Atribución - No Comercial - Sin Derivadas (CC - By-NC-ND 4.0) |
| dc.rights.none.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.source.none.fl_str_mv | reponame:COLIBRI instname:Universidad de la República instacron:Universidad de la República |
| dc.subject.es.fl_str_mv | CARBOHIDRATOS INMINOAZUCAR TRYPANOSOMA BRUCEI REACCION DE MANNICH ORGANOCATALISIS |
| dc.title.none.fl_str_mv | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| dc.type.es.fl_str_mv | Artículo |
| dc.type.none.fl_str_mv | info:eu-repo/semantics/article |
| dc.type.version.none.fl_str_mv | info:eu-repo/semantics/publishedVersion |
| description | Versión aceptada (Postprint) |
| eu_rights_str_mv | openAccess |
| format | article |
| id | COLIBRI_f0853a52dbece5e4ac8d19915b34de38 |
| identifier_str_mv | Mesa, J, Comini, M, Dibello, E y Gamenara, D. "Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars". European Journal of Organic Chemistry. [en línea] 2022 v.34, 2022. -- e202200636 .. 7 p.. 10.1002/ejoc.202200636 |
| instacron_str | Universidad de la República |
| institution | Universidad de la República |
| instname_str | Universidad de la República |
| language | eng |
| language_invalid_str_mv | en |
| network_acronym_str | COLIBRI |
| network_name_str | COLIBRI |
| oai_identifier_str | oai:colibri.udelar.edu.uy:20.500.12008/36737 |
| publishDate | 2022 |
| reponame_str | COLIBRI |
| repository.mail.fl_str_mv | karina.camps@seciu.edu.uy |
| repository.name.fl_str_mv | COLIBRI - Universidad de la República |
| repository_id_str | 4771 |
| rights_invalid_str_mv | Licencia Creative Commons Atribución - No Comercial - Sin Derivadas (CC - By-NC-ND 4.0) |
| spelling | Mesa Juan M. Universidad de la República (Uruguay). Facultad de Química. Departamento de Química OrgánicaComini Marcelo A. Instituto Pasteur (Uruguay). Grupo Biología Redox de TripanosomátidosDibello Estefanía. Universidad de la República (Uruguay). Facultad de Química. Departamento de Química Orgánica ; Instituto Pasteur (Uruguay). Grupo Biología Redox de TripanosomátidosGamenara Daniela2023-04-19T13:42:01Z2023-04-19T13:42:01Z2022Mesa, J, Comini, M, Dibello, E y Gamenara, D. "Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars". European Journal of Organic Chemistry. [en línea] 2022 v.34, 2022. -- e202200636 .. 7 p..https://hdl.handle.net/20.500.12008/3673710.1002/ejoc.202200636Versión aceptada (Postprint)A series of L-lyxo and L-xylo- pentofuranose-mimetic iminosugars and derivatives were efficiently synthesized in a stereoselective manner, through a concise strategy which involves an organocatalyzed Mannich reaction of an imine and a protected dioxanone as key step, using D-proline as catalyst. A preliminary evaluation of their activity as potential anti-trypanosomal agents was studied. One of the synthesized compounds showed an interesting activity against bloodstream Trypanosoma brucei brucei (EC,)=3.8 + 1.0 1M).Submitted by Cabrera Jeniffer (jenikana@gmail.com) on 2023-04-19T12:39:07Z No. of bitstreams: 2 license_rdf: 23149 bytes, checksum: 1996b8461bc290aef6a27d78c67b6b52 (MD5) Eur J Org Chem_2022_Mesa.pdf: 1093455 bytes, checksum: 3fa5f98b6682177cc1444ce3ad926aac (MD5)Made available in DSpace by Luna Fabiana (fabiana.luna@seciu.edu.uy) on 2023-04-19T13:42:01Z (GMT). No. of bitstreams: 2 license_rdf: 23149 bytes, checksum: 1996b8461bc290aef6a27d78c67b6b52 (MD5) Eur J Org Chem_2022_Mesa.pdf: 1093455 bytes, checksum: 3fa5f98b6682177cc1444ce3ad926aac (MD5) Previous issue date: 20227 p.application/pdfenengWileyEuropean Journal of Organic Chemistry, v.34, 2022. -- e202200636Las obras depositadas en el Repositorio se rigen por la Ordenanza de los Derechos de la Propiedad Intelectual de la Universidad de la República.(Res. Nº 91 de C.D.C. de 8/III/1994 – D.O. 7/IV/1994) y por la Ordenanza del Repositorio Abierto de la Universidad de la República (Res. Nº 16 de C.D.C. de 07/10/2014)info:eu-repo/semantics/openAccessLicencia Creative Commons Atribución - No Comercial - Sin Derivadas (CC - By-NC-ND 4.0)CARBOHIDRATOSINMINOAZUCARTRYPANOSOMA BRUCEIREACCION DE MANNICHORGANOCATALISISOrganocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugarsArtículoinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionreponame:COLIBRIinstname:Universidad de la Repúblicainstacron:Universidad de la RepúblicaMesa, Juan M.Comini, Marcelo A.Dibello, EstefaníaGamenara, DanielaLICENSElicense.txtlicense.txttext/plain; charset=utf-84267http://localhost:8080/xmlui/bitstream/20.500.12008/36737/5/license.txt6429389a7df7277b72b7924fdc7d47a9MD55CC-LICENSElicense_urllicense_urltext/plain; charset=utf-850http://localhost:8080/xmlui/bitstream/20.500.12008/36737/2/license_urla006180e3f5b2ad0b88185d14284c0e0MD52license_textlicense_texttext/html; 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- Universidad de la Repúblicafalse |
| spellingShingle | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars Mesa, Juan M. CARBOHIDRATOS INMINOAZUCAR TRYPANOSOMA BRUCEI REACCION DE MANNICH ORGANOCATALISIS |
| status_str | publishedVersion |
| title | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| title_full | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| title_fullStr | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| title_full_unstemmed | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| title_short | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| title_sort | Organocatalytic synthesis and Anti-Trypanosomal activity evaluation of L-Pentofuranose-Mimetic iminosugars |
| topic | CARBOHIDRATOS INMINOAZUCAR TRYPANOSOMA BRUCEI REACCION DE MANNICH ORGANOCATALISIS |
| url | https://hdl.handle.net/20.500.12008/36737 |
