Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents
Autor(a) principal: | |
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Data de Publicação: | 2024 |
Tipo de documento: | Dissertação |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFPE |
Texto Completo: | https://repositorio.ufpe.br/handle/123456789/56215 |
Resumo: | Tuberculosis is a disease that still brings risks to global health since resistance to existing drugs promotes the search for new treatments. The aim of this study was therefore to synthesize new glycero-carbohydrates conjugated to thio-heterocycles and evaluate its biological profile against tuberculosis. We first synthesized glycerol derivatives: glycerol carbonate 1 (96%), tosylated glycerol carbonate 2 (65%), glycerol iodo-carbonate 3 (80%) and glycerol thio-carbonate 4 (85%). The (R) azido-alcohol 7a was previously prepared by our research group, as was the mixture of diastereoisomers of the 2,3-unsaturated O-glycosides 6a/6b which was used to prepare the keto-azide 8, with a yield of 88%. In another synthetic strategy, we protected tri-O-acetyl-D-glucal 5 with (Z)-1,2-bis(phenylsulfonyl)ethylene (BPSE) 9 to obtain PSE-glucal 10 (77%). The double bond epoxidation reaction of PSE-glucal 10 with m-CPBA stereoselectively provided the unprecedented α-mannopyranoside 11 in 52% yield, and after acetylation under acidic conditions (K-10) we obtained α- mannopyranoside 12 (77%). The aglycone portion of α-mannopyranoside 12 was also replaced by the glycerol carbonate ring, and the unprecedented R/S mixture of β- mannopyranoside 13 was obtained in 64% yield. In the glycosylation reaction under Ferrier conditions between PSE-glucal 10 and glycerol carbonate 1, was observed the formation of a complex mixture 14a and the mixture R/S of the new α-2-deoxy-O- glucoside isomer 14b with yields of 33% and 42%, as a result of a Michael addition reaction. The new heterocycles 1,3-oxazolidine-2-thione 16a and 1,3-thiazolidine-2- thione 16b were synthesized from (R) azido-alcohol 7a using CS2 and PPh3, with yields of 22% and 39%, respectively. 2-mercapto-oxazole 17 (59%) was prepared from the reaction of keto-azide 8 in the presence of CS2 and PPh3 as well. Finally, in the biological study, thio-derivatives 16a, 16b and 17 didn’t show any activity against tuberculosis, however, they weren’t considered toxic to the cells tested. |
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SILVA, Carla Jasmine Oliveira ehttp://lattes.cnpq.br/6278050350925332http://lattes.cnpq.br/9071551767043294OLIVEIRA, Ronaldo Nascimento deTATIBOUET, Arnaud2024-05-06T19:40:38Z2024-05-06T19:40:38Z2024-01-30SILVA, Carla Jasmine Oliveira e. Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents. 2024. Dissertação (Mestrado em Química) – Universidade Federal de Pernambuco, Recife, 2024.https://repositorio.ufpe.br/handle/123456789/56215Tuberculosis is a disease that still brings risks to global health since resistance to existing drugs promotes the search for new treatments. The aim of this study was therefore to synthesize new glycero-carbohydrates conjugated to thio-heterocycles and evaluate its biological profile against tuberculosis. We first synthesized glycerol derivatives: glycerol carbonate 1 (96%), tosylated glycerol carbonate 2 (65%), glycerol iodo-carbonate 3 (80%) and glycerol thio-carbonate 4 (85%). The (R) azido-alcohol 7a was previously prepared by our research group, as was the mixture of diastereoisomers of the 2,3-unsaturated O-glycosides 6a/6b which was used to prepare the keto-azide 8, with a yield of 88%. In another synthetic strategy, we protected tri-O-acetyl-D-glucal 5 with (Z)-1,2-bis(phenylsulfonyl)ethylene (BPSE) 9 to obtain PSE-glucal 10 (77%). The double bond epoxidation reaction of PSE-glucal 10 with m-CPBA stereoselectively provided the unprecedented α-mannopyranoside 11 in 52% yield, and after acetylation under acidic conditions (K-10) we obtained α- mannopyranoside 12 (77%). The aglycone portion of α-mannopyranoside 12 was also replaced by the glycerol carbonate ring, and the unprecedented R/S mixture of β- mannopyranoside 13 was obtained in 64% yield. In the glycosylation reaction under Ferrier conditions between PSE-glucal 10 and glycerol carbonate 1, was observed the formation of a complex mixture 14a and the mixture R/S of the new α-2-deoxy-O- glucoside isomer 14b with yields of 33% and 42%, as a result of a Michael addition reaction. The new heterocycles 1,3-oxazolidine-2-thione 16a and 1,3-thiazolidine-2- thione 16b were synthesized from (R) azido-alcohol 7a using CS2 and PPh3, with yields of 22% and 39%, respectively. 2-mercapto-oxazole 17 (59%) was prepared from the reaction of keto-azide 8 in the presence of CS2 and PPh3 as well. Finally, in the biological study, thio-derivatives 16a, 16b and 17 didn’t show any activity against tuberculosis, however, they weren’t considered toxic to the cells tested.FACEPEA tuberculose é uma doença que ainda traz riscos à saúde global, uma vez que a resistência aos medicamentos já existentes impulsiona a busca pelo desenvolvimento de novos tratamentos. Dessa forma, o objetivo do presente trabalho foi sintetizar novos glicero-carboidratos conjugados com tio-heterociclos e avaliar seu perfil biológico contra a tuberculose. Num primeiro momento, realizamos a síntese dos derivados do glicerol: carbonato de glicerol 1 (96%), carbonato de glicerol tosilado 2 (65%), iodo-carbonato de glicerol 3 (80%) e tio-carbonato de glicerol 4 (85%). O (R) azido-álcool 7a foi previamente preparado pelo nosso grupo de pesquisa, bem como a mistura de diastereoisômeros dos O-glicosídeos 2,3-insaturados 6a/6b que foi utilizada para preparar a ceto-azida 8, com rendimento de 88%. Em outra estratégia sintética, realizamos a proteção do tri-O-acetil-D-glucal 5 com o (Z)-1,2- bis(fenilsulfonil)etileno (BPSE) 9 para obter o PSE-glical 10 (77%). A reação de epoxidação na dupla ligação do PSE-glical 10 com o m-CPBA forneceu estereosseletivamente o α-manopiranosídeo 11 inédito com 52% de rendimento, e após reação de acetilação em condições ácidas (k-10) obtivemos o α- manopiranosídeo 12 (77%). Também foi realizada a substituição da porção aglicona α-manopiranosídeo 12 pelo anel do carbonato de glicerol, a mistura R/S do novo β- manopiranosídeo 13 foi obtida com rendimento de 64%. Na reação de glicosilação sob condições de Ferrier entre o PSE-glical 10 e o carbonato de glicerol 1, observamos a formação de uma mistura complexa 14a e da mistura R/S do novo isômero α-2- desoxi-O-glicosídeo 14b com rendimentos de 33% e 42%, como resultado de uma reação de adição de Michael. Posteriormente, realizou-se a síntese dos novos heterociclos 1,3-oxazolidina-2-tiona 16a e 1,3-tiazolidina-2-tiona 16b a partir do (R) azido-álcool 7a com CS2 e PPh3, com rendimentos de 22% e 39%, respectivamente. O 2-mercapto-oxazol 17 (59%) foi preparado a partir da reação da ceto-azida 8 na presença de CS2 e PPh3 também. Por fim, no que diz respeito ao estudo biológico, os tio-derivados 16a, 16b, e 17 não apresentaram atividade contra tuberculose, no entanto, não foram considerados tóxicos para as células testadas.engUniversidade Federal de PernambucoPrograma de Pos Graduacao em QuimicaUFPEBrasilAttribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessGlicoconjugadosGlicerolFenilsulfoniletilideno (PSE) acetaloxazolidinationaTiazolidinationaOxazolSynthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agentsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesismestradoreponame:Repositório Institucional da UFPEinstname:Universidade Federal de Pernambuco (UFPE)instacron:UFPECC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8811https://repositorio.ufpe.br/bitstream/123456789/56215/2/license_rdfe39d27027a6cc9cb039ad269a5db8e34MD52ORIGINALDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdfDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdfapplication/pdf4395123https://repositorio.ufpe.br/bitstream/123456789/56215/1/DISSERTA%c3%87%c3%83O%20Carla%20Jasmine%20Oliveira%20e%20Silva.pdf509d5fac366dc50e9a0de408b0ad5605MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-82362https://repositorio.ufpe.br/bitstream/123456789/56215/3/license.txt5e89a1613ddc8510c6576f4b23a78973MD53TEXTDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdf.txtDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdf.txtExtracted texttext/plain205018https://repositorio.ufpe.br/bitstream/123456789/56215/4/DISSERTA%c3%87%c3%83O%20Carla%20Jasmine%20Oliveira%20e%20Silva.pdf.txta509b22a9169e51570aec930a5f54978MD54THUMBNAILDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdf.jpgDISSERTAÇÃO Carla Jasmine Oliveira e Silva.pdf.jpgGenerated Thumbnailimage/jpeg1271https://repositorio.ufpe.br/bitstream/123456789/56215/5/DISSERTA%c3%87%c3%83O%20Carla%20Jasmine%20Oliveira%20e%20Silva.pdf.jpg5b1d5340ce6396310fdb65228fa805d0MD55123456789/562152024-05-07 02:25:44.791oai:repositorio.ufpe.br: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Repositório InstitucionalPUBhttps://repositorio.ufpe.br/oai/requestattena@ufpe.bropendoar:22212024-05-07T05:25:44Repositório Institucional da UFPE - Universidade Federal de Pernambuco (UFPE)false |
dc.title.pt_BR.fl_str_mv |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
title |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
spellingShingle |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents SILVA, Carla Jasmine Oliveira e Glicoconjugados Glicerol Fenilsulfoniletilideno (PSE) acetal oxazolidinationa Tiazolidinationa Oxazol |
title_short |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
title_full |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
title_fullStr |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
title_full_unstemmed |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
title_sort |
Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents |
author |
SILVA, Carla Jasmine Oliveira e |
author_facet |
SILVA, Carla Jasmine Oliveira e |
author_role |
author |
dc.contributor.authorLattes.pt_BR.fl_str_mv |
http://lattes.cnpq.br/6278050350925332 |
dc.contributor.advisorLattes.pt_BR.fl_str_mv |
http://lattes.cnpq.br/9071551767043294 |
dc.contributor.author.fl_str_mv |
SILVA, Carla Jasmine Oliveira e |
dc.contributor.advisor1.fl_str_mv |
OLIVEIRA, Ronaldo Nascimento de |
dc.contributor.advisor-co1.fl_str_mv |
TATIBOUET, Arnaud |
contributor_str_mv |
OLIVEIRA, Ronaldo Nascimento de TATIBOUET, Arnaud |
dc.subject.por.fl_str_mv |
Glicoconjugados Glicerol Fenilsulfoniletilideno (PSE) acetal oxazolidinationa Tiazolidinationa Oxazol |
topic |
Glicoconjugados Glicerol Fenilsulfoniletilideno (PSE) acetal oxazolidinationa Tiazolidinationa Oxazol |
description |
Tuberculosis is a disease that still brings risks to global health since resistance to existing drugs promotes the search for new treatments. The aim of this study was therefore to synthesize new glycero-carbohydrates conjugated to thio-heterocycles and evaluate its biological profile against tuberculosis. We first synthesized glycerol derivatives: glycerol carbonate 1 (96%), tosylated glycerol carbonate 2 (65%), glycerol iodo-carbonate 3 (80%) and glycerol thio-carbonate 4 (85%). The (R) azido-alcohol 7a was previously prepared by our research group, as was the mixture of diastereoisomers of the 2,3-unsaturated O-glycosides 6a/6b which was used to prepare the keto-azide 8, with a yield of 88%. In another synthetic strategy, we protected tri-O-acetyl-D-glucal 5 with (Z)-1,2-bis(phenylsulfonyl)ethylene (BPSE) 9 to obtain PSE-glucal 10 (77%). The double bond epoxidation reaction of PSE-glucal 10 with m-CPBA stereoselectively provided the unprecedented α-mannopyranoside 11 in 52% yield, and after acetylation under acidic conditions (K-10) we obtained α- mannopyranoside 12 (77%). The aglycone portion of α-mannopyranoside 12 was also replaced by the glycerol carbonate ring, and the unprecedented R/S mixture of β- mannopyranoside 13 was obtained in 64% yield. In the glycosylation reaction under Ferrier conditions between PSE-glucal 10 and glycerol carbonate 1, was observed the formation of a complex mixture 14a and the mixture R/S of the new α-2-deoxy-O- glucoside isomer 14b with yields of 33% and 42%, as a result of a Michael addition reaction. The new heterocycles 1,3-oxazolidine-2-thione 16a and 1,3-thiazolidine-2- thione 16b were synthesized from (R) azido-alcohol 7a using CS2 and PPh3, with yields of 22% and 39%, respectively. 2-mercapto-oxazole 17 (59%) was prepared from the reaction of keto-azide 8 in the presence of CS2 and PPh3 as well. Finally, in the biological study, thio-derivatives 16a, 16b and 17 didn’t show any activity against tuberculosis, however, they weren’t considered toxic to the cells tested. |
publishDate |
2024 |
dc.date.accessioned.fl_str_mv |
2024-05-06T19:40:38Z |
dc.date.available.fl_str_mv |
2024-05-06T19:40:38Z |
dc.date.issued.fl_str_mv |
2024-01-30 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SILVA, Carla Jasmine Oliveira e. Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents. 2024. Dissertação (Mestrado em Química) – Universidade Federal de Pernambuco, Recife, 2024. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufpe.br/handle/123456789/56215 |
identifier_str_mv |
SILVA, Carla Jasmine Oliveira e. Synthesis of thio-derivatives conjugated to glycero-carbohydrates and their potential as anti-tuberculosis agents. 2024. Dissertação (Mestrado em Química) – Universidade Federal de Pernambuco, Recife, 2024. |
url |
https://repositorio.ufpe.br/handle/123456789/56215 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Pernambuco |
dc.publisher.program.fl_str_mv |
Programa de Pos Graduacao em Quimica |
dc.publisher.initials.fl_str_mv |
UFPE |
dc.publisher.country.fl_str_mv |
Brasil |
publisher.none.fl_str_mv |
Universidade Federal de Pernambuco |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFPE instname:Universidade Federal de Pernambuco (UFPE) instacron:UFPE |
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Universidade Federal de Pernambuco (UFPE) |
instacron_str |
UFPE |
institution |
UFPE |
reponame_str |
Repositório Institucional da UFPE |
collection |
Repositório Institucional da UFPE |
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