Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis

Detalhes bibliográficos
Autor(a) principal: Facchinetti, Victor
Data de Publicação: 2018
Outros Autores: Souza, Marcus V. N. de, Nery, Ana C. S., Calixto, Stephane L., Granato, Juliana T., Coimbra, Elaine S., Lourenço, Maria C. S., Gomes, Claudia R. B., Vasconcelos, Thatyana R. A.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/33776
Resumo: 2020-07-02
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spelling Facchinetti, VictorSouza, Marcus V. N. deNery, Ana C. S.Calixto, Stephane L.Granato, Juliana T.Coimbra, Elaine S.Lourenço, Maria C. S.Gomes, Claudia R. B.Vasconcelos, Thatyana R. A.2019-07-02T14:38:19Z2019-07-02T14:38:19Z2018FACCHINETTI, Victor et al. Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis. Letters in Drug Design and Discovery, v. 15, n. 11, p. 1-6, 2018.1570-1808https://www.arca.fiocruz.br/handle/icict/3377610.2174/15701808156661802091539251875-628XengBentham Science PublishersSynthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-07-02Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Programa de Pós-Graduação em Química. Niterói. RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Universidade Federal de Juiz de Fora. Instituto de Ciências Biológicas. Departamento de Parasitologia Microbiologia e Imunologia. Juiz de Fora, MG, Brasil.Universidade Federal de Juiz de Fora. Instituto de Ciências Biológicas. Departamento de Parasitologia Microbiologia e Imunologia. Juiz de Fora, MG, Brasil.Universidade Federal de Juiz de Fora. Instituto de Ciências Biológicas. Departamento de Parasitologia Microbiologia e Imunologia. Juiz de Fora, MG, Brasil.Fundação Oswaldo Cruz. Instituto Nacional de Infectologia Evandro Chagas. Serviço de Bacteriologia. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica. Programa de Pós-Graduação em Química. Niterói. RJ, Brasil.Background: 2-aminoselenazoles became an important core in medicinal chemistry after the discovery of Ebselen and Ethaselen. Therefore, many researchers have reported the synthesis of small selenazole intermediates via Hantzsch cyclization using a wide array of methodologies andcatalysts. Methods: In this work, we investigated the formation of 2-aminoselenazoles on various organic solvents and in water, under catalyst-free conditions. Moreover, these molecules and their 2-aminothiazoles analogues were assessed in vitro for their antitubercular activity against Mycobacterium tuberculosis and the results compared. Results: Instant reactions were observed when using polar aprotic solvents and all selenazoles were synthesized in water using sonochemistry. Furthermore, two selenazoles and one thiazole displayed activity in the μM range and the selenium heterocycles seems to be more potent than their sulphur analogues. Conclusion: This is the first study of selenazoles against M. tuberculosis. It is noteworthy that 2-amino-1,3-selenazoles are interesting synthetic intermediates that could be incorporated into novel prototypes against tuberculosis.TuberculosisSelenazoleSynthesisMethodologyUltrasoundHantzsch cyclizationinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/33776/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Facchinetti_Victor_etal_INI_2018.pdfve_Facchinetti_Victor_etal_INI_2018.pdfapplication/pdf2328211https://www.arca.fiocruz.br/bitstream/icict/33776/2/ve_Facchinetti_Victor_etal_INI_2018.pdf7d9af3add5444d5aa8390852ac232adbMD52TEXTve_Facchinetti_Victor_etal_INI_2018.pdf.txtve_Facchinetti_Victor_etal_INI_2018.pdf.txtExtracted texttext/plain29196https://www.arca.fiocruz.br/bitstream/icict/33776/3/ve_Facchinetti_Victor_etal_INI_2018.pdf.txtd1684942586ed09d175431b4e82b0595MD53icict/337762021-03-24 16:32:33.903oai:www.arca.fiocruz.br:icict/33776Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:33Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
title Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
spellingShingle Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
Facchinetti, Victor
Tuberculosis
Selenazole
Synthesis
Methodology
Ultrasound
Hantzsch cyclization
title_short Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
title_full Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
title_fullStr Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
title_full_unstemmed Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
title_sort Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis
author Facchinetti, Victor
author_facet Facchinetti, Victor
Souza, Marcus V. N. de
Nery, Ana C. S.
Calixto, Stephane L.
Granato, Juliana T.
Coimbra, Elaine S.
Lourenço, Maria C. S.
Gomes, Claudia R. B.
Vasconcelos, Thatyana R. A.
author_role author
author2 Souza, Marcus V. N. de
Nery, Ana C. S.
Calixto, Stephane L.
Granato, Juliana T.
Coimbra, Elaine S.
Lourenço, Maria C. S.
Gomes, Claudia R. B.
Vasconcelos, Thatyana R. A.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Facchinetti, Victor
Souza, Marcus V. N. de
Nery, Ana C. S.
Calixto, Stephane L.
Granato, Juliana T.
Coimbra, Elaine S.
Lourenço, Maria C. S.
Gomes, Claudia R. B.
Vasconcelos, Thatyana R. A.
dc.subject.en.pt_BR.fl_str_mv Tuberculosis
Selenazole
Synthesis
Methodology
Ultrasound
Hantzsch cyclization
topic Tuberculosis
Selenazole
Synthesis
Methodology
Ultrasound
Hantzsch cyclization
description 2020-07-02
publishDate 2018
dc.date.issued.fl_str_mv 2018
dc.date.accessioned.fl_str_mv 2019-07-02T14:38:19Z
dc.date.available.fl_str_mv 2019-07-02T14:38:19Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv FACCHINETTI, Victor et al. Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis. Letters in Drug Design and Discovery, v. 15, n. 11, p. 1-6, 2018.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/33776
dc.identifier.issn.pt_BR.fl_str_mv 1570-1808
dc.identifier.doi.none.fl_str_mv 10.2174/1570180815666180209153925
dc.identifier.eissn.none.fl_str_mv 1875-628X
identifier_str_mv FACCHINETTI, Victor et al. Synthetic aspects and first-time assessment of 2-amino-1,3-selenazoles against Mycobacterium tuberculosis. Letters in Drug Design and Discovery, v. 15, n. 11, p. 1-6, 2018.
1570-1808
10.2174/1570180815666180209153925
1875-628X
url https://www.arca.fiocruz.br/handle/icict/33776
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
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