Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents

ABSTARCT: The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the...

Full description

Autores:
Vélez Bernal, Iván Darío
Robledo Restrepo, Sara María
Echeverri López, Luis Fernando
Quiñones Fletcher, Winston
Tipo de recurso:
Article of investigation
Fecha de publicación:
2017
Institución:
Universidad de Antioquia
Repositorio:
Repositorio UdeA
Idioma:
eng
OAI Identifier:
oai:bibliotecadigital.udea.edu.co:10495/11589
Acceso en línea:
http://hdl.handle.net/10495/11589
Palabra clave:
Leishmania
Thiochroman-4-one
Thiochromones
Thioflavone
Vinyl sulfone
Rights
openAccess
License
Atribución 2.5
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oai_identifier_str oai:bibliotecadigital.udea.edu.co:10495/11589
network_acronym_str UDEA2
network_name_str Repositorio UdeA
repository_id_str
dc.title.spa.fl_str_mv Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
title Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
spellingShingle Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
Leishmania
Thiochroman-4-one
Thiochromones
Thioflavone
Vinyl sulfone
title_short Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
title_full Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
title_fullStr Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
title_full_unstemmed Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
title_sort Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
dc.creator.fl_str_mv Vélez Bernal, Iván Darío
Robledo Restrepo, Sara María
Echeverri López, Luis Fernando
Quiñones Fletcher, Winston
dc.contributor.author.none.fl_str_mv Vélez Bernal, Iván Darío
Robledo Restrepo, Sara María
Echeverri López, Luis Fernando
Quiñones Fletcher, Winston
dc.subject.none.fl_str_mv Leishmania
Thiochroman-4-one
Thiochromones
Thioflavone
Vinyl sulfone
topic Leishmania
Thiochroman-4-one
Thiochromones
Thioflavone
Vinyl sulfone
description ABSTARCT: The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.
publishDate 2017
dc.date.issued.none.fl_str_mv 2017
dc.date.accessioned.none.fl_str_mv 2019-07-31T20:50:57Z
dc.date.available.none.fl_str_mv 2019-07-31T20:50:57Z
dc.type.spa.fl_str_mv info:eu-repo/semantics/article
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dc.type.local.spa.fl_str_mv Artículo de investigación
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dc.identifier.citation.spa.fl_str_mv Vargas E, Echeverri F, Vélez ID, Robledo SM, Quiñones W. Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents. Molecules. 2017 Nov 29;22(12). pii: E2041
dc.identifier.issn.none.fl_str_mv 1420-3049
dc.identifier.uri.none.fl_str_mv http://hdl.handle.net/10495/11589
dc.identifier.doi.none.fl_str_mv 10.3390/molecules22122041
identifier_str_mv Vargas E, Echeverri F, Vélez ID, Robledo SM, Quiñones W. Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents. Molecules. 2017 Nov 29;22(12). pii: E2041
1420-3049
10.3390/molecules22122041
url http://hdl.handle.net/10495/11589
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.ispartofjournalabbrev.spa.fl_str_mv Molecules
dc.rights.*.fl_str_mv Atribución 2.5
dc.rights.spa.fl_str_mv info:eu-repo/semantics/openAccess
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dc.rights.creativecommons.spa.fl_str_mv https://creativecommons.org/licenses/by/4.0/
rights_invalid_str_mv Atribución 2.5
http://creativecommons.org/licenses/by/2.5/co/
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
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dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv MDPI
dc.publisher.group.spa.fl_str_mv Programa de Estudio y Control de Enfermedades Tropicales (PECET)
Quimica Organica de Productos Naturales
dc.publisher.place.spa.fl_str_mv Suiza
institution Universidad de Antioquia
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spelling Vélez Bernal, Iván DaríoRobledo Restrepo, Sara MaríaEcheverri López, Luis FernandoQuiñones Fletcher, Winston2019-07-31T20:50:57Z2019-07-31T20:50:57Z2017Vargas E, Echeverri F, Vélez ID, Robledo SM, Quiñones W. Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents. Molecules. 2017 Nov 29;22(12). pii: E20411420-3049http://hdl.handle.net/10495/1158910.3390/molecules22122041ABSTARCT: The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.0application/pdfengMDPIPrograma de Estudio y Control de Enfermedades Tropicales (PECET)Quimica Organica de Productos NaturalesSuizainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85Atribución 2.5info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by/4.0/LeishmaniaThiochroman-4-oneThiochromonesThioflavoneVinyl sulfoneSynthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal AgentsMoleculesMolecules16162922ORIGINALVargasEsteban_2017_SynthesisEvaluationThiocharoman.pdfVargasEsteban_2017_SynthesisEvaluationThiocharoman.pdfArtículo de Revistaapplication/pdf1259406http://bibliotecadigital.udea.edu.co/bitstream/10495/11589/1/VargasEsteban_2017_SynthesisEvaluationThiocharoman.pdfb80359a5dfa0a5ec0d6ee147a973f50aMD51CC-LICENSElicense_urllicense_urltext/plain; charset=utf-849http://bibliotecadigital.udea.edu.co/bitstream/10495/11589/2/license_url4afdbb8c545fd630ea7db775da747b2fMD52license_textlicense_texttext/html; charset=utf-80http://bibliotecadigital.udea.edu.co/bitstream/10495/11589/3/license_textd41d8cd98f00b204e9800998ecf8427eMD53license_rdflicense_rdfapplication/rdf+xml; charset=utf-80http://bibliotecadigital.udea.edu.co/bitstream/10495/11589/4/license_rdfd41d8cd98f00b204e9800998ecf8427eMD54LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://bibliotecadigital.udea.edu.co/bitstream/10495/11589/5/license.txt8a4605be74aa9ea9d79846c1fba20a33MD5510495/11589oai:bibliotecadigital.udea.edu.co:10495/115892021-03-24 21:43:08.603Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.coTk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=

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