Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2020 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/43092 |
Resumo: | University of Bristol. School of Chemistry. Bristol, UK. |
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Wood, James M.Satam, Nishikant S.Almeida, Renata G.Cristani, Vinicius S.Lima, Dênis P. dePereira, Luiza DantasSalomão, KellyMenna-Barreto, Rubem .F S.Namboothiri, Irishi N. N.Bower, John F.Silva Júnior, Eufrânio N. da2020-08-31T20:08:28Z2020-08-31T20:08:28Z2020WOOD, James M. et al. Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi. Biorganic & Medicinal Chemistry, v. 28, 115565, 11p, May 2020.0968-0896https://www.arca.fiocruz.br/handle/icict/4309210.1016/j.bmc.2020.115565engElsevierDoença de ChagasQuinonesAnulaçãoNitroalquenosCicloadições [2 + 2 + 2] catalisadas por RhQuinonesChagas diseaseRh-catalyzed [2 + 2 + 2] cycloadditionsAnnulationNitroalkenesStrategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruziinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversity of Bristol. School of Chemistry. Bristol, UK.Indian Institute of Technology Bombay. Department of Chemistry. Mumbai, India.Universidade Federal de Minas Gerais. Insituto de Ciências Extas. Departamento de Química. Belo Horizonte, MG, Brasil.Universidade Federal de Mato Grosso do Sul. Insituto de Química. Campo Grande, MS, Brasil.Universidade Federal de Mato Grosso do Sul. Insituto de Química. Campo Grande, MS, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia. Rio de Janeiro, RJ, Brasil.Indian Institute of Technology Bombay. Department of Chemistry. Mumbai, India.University of Bristol. School of Chemistry. Bristol, UK / University of Liverpool, Department Chemistry. Liverpool, United Kingdom.Universidade Federal de Minas Gerais. Insituto de Ciências Extas. Departamento de Química. Belo Horizonte, MG, Brasil.Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/43092/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALRubenFSMennaBarreto_LuizaDPereira_etal_IOC_2020.pdfRubenFSMennaBarreto_LuizaDPereira_etal_IOC_2020.pdfapplication/pdf2490496https://www.arca.fiocruz.br/bitstream/icict/43092/2/RubenFSMennaBarreto_LuizaDPereira_etal_IOC_2020.pdf5953c25eba8da523cf572822c171174aMD52TEXTRubenFSMennaBarreto_LuizaDPereira_etal_IOC_2020.pdf.txtRubenFSMennaBarreto_LuizaDPereira_etal_IOC_2020.pdf.txtExtracted 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| dc.title.pt_BR.fl_str_mv |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| title |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| spellingShingle |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi Wood, James M. Doença de Chagas Quinones Anulação Nitroalquenos Cicloadições [2 + 2 + 2] catalisadas por Rh Quinones Chagas disease Rh-catalyzed [2 + 2 + 2] cycloadditions Annulation Nitroalkenes |
| title_short |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| title_full |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| title_fullStr |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| title_full_unstemmed |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| title_sort |
Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi |
| author |
Wood, James M. |
| author_facet |
Wood, James M. Satam, Nishikant S. Almeida, Renata G. Cristani, Vinicius S. Lima, Dênis P. de Pereira, Luiza Dantas Salomão, Kelly Menna-Barreto, Rubem .F S. Namboothiri, Irishi N. N. Bower, John F. Silva Júnior, Eufrânio N. da |
| author_role |
author |
| author2 |
Satam, Nishikant S. Almeida, Renata G. Cristani, Vinicius S. Lima, Dênis P. de Pereira, Luiza Dantas Salomão, Kelly Menna-Barreto, Rubem .F S. Namboothiri, Irishi N. N. Bower, John F. Silva Júnior, Eufrânio N. da |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Wood, James M. Satam, Nishikant S. Almeida, Renata G. Cristani, Vinicius S. Lima, Dênis P. de Pereira, Luiza Dantas Salomão, Kelly Menna-Barreto, Rubem .F S. Namboothiri, Irishi N. N. Bower, John F. Silva Júnior, Eufrânio N. da |
| dc.subject.other.pt_BR.fl_str_mv |
Doença de Chagas Quinones Anulação Nitroalquenos Cicloadições [2 + 2 + 2] catalisadas por Rh |
| topic |
Doença de Chagas Quinones Anulação Nitroalquenos Cicloadições [2 + 2 + 2] catalisadas por Rh Quinones Chagas disease Rh-catalyzed [2 + 2 + 2] cycloadditions Annulation Nitroalkenes |
| dc.subject.en.pt_BR.fl_str_mv |
Quinones Chagas disease Rh-catalyzed [2 + 2 + 2] cycloadditions Annulation Nitroalkenes |
| description |
University of Bristol. School of Chemistry. Bristol, UK. |
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2020 |
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2020-08-31T20:08:28Z |
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2020-08-31T20:08:28Z |
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2020 |
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info:eu-repo/semantics/article |
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WOOD, James M. et al. Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi. Biorganic & Medicinal Chemistry, v. 28, 115565, 11p, May 2020. |
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https://www.arca.fiocruz.br/handle/icict/43092 |
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0968-0896 |
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10.1016/j.bmc.2020.115565 |
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WOOD, James M. et al. Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi. Biorganic & Medicinal Chemistry, v. 28, 115565, 11p, May 2020. 0968-0896 10.1016/j.bmc.2020.115565 |
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