1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Brazilian Journal of Pharmaceutical Sciences |
Texto Completo: | https://www.revistas.usp.br/bjps/article/view/131425 |
Resumo: | Dramatically increased occurrence of both superficial and invasive fungal infections has been observed. Candida albicans appear to be the main etiological agent of invasive fungal infections. The anti-C. albicans activity of thiosemicarbazide, 1,3,4-Thiadiazole, and 1,2,4-triazole-3(4H)-thione compounds (compounds 3-23) were investigated. The MIC values of thiadiazole and triazole derivatives 10-23 were in the range of 0.08-0.17 µmol mL-1, while that of fluconazole was 0.052 µmol mL-1. Compound 11 (5-(2-(4-chlorobenzyloxy)phenyl)-N-allyl-1,3,4-thiadiazol-2-amine) and compound 18 (5-(2-(4-chlorobenzyloxy)phenyl)-4-allyl-2H-1,2,4-triazole-3(4H)-thione) were found to be the most active compounds, with MIC values of 0.08 µmol mL-1. The newly synthesized thiadiazole and triazole compounds (compounds 10-23) showed promising anti-Candida activity. The allyl substituent-bearing compounds 11 and 18 exhibited significant anti-Candida albicans activity and showed a binding mode as well as the fluconazole x-ray structure. |
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Brazilian Journal of Pharmaceutical Sciences |
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1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicansAnti-Candida/docking studiesThiadiazoleTriazoleDramatically increased occurrence of both superficial and invasive fungal infections has been observed. Candida albicans appear to be the main etiological agent of invasive fungal infections. The anti-C. albicans activity of thiosemicarbazide, 1,3,4-Thiadiazole, and 1,2,4-triazole-3(4H)-thione compounds (compounds 3-23) were investigated. The MIC values of thiadiazole and triazole derivatives 10-23 were in the range of 0.08-0.17 µmol mL-1, while that of fluconazole was 0.052 µmol mL-1. Compound 11 (5-(2-(4-chlorobenzyloxy)phenyl)-N-allyl-1,3,4-thiadiazol-2-amine) and compound 18 (5-(2-(4-chlorobenzyloxy)phenyl)-4-allyl-2H-1,2,4-triazole-3(4H)-thione) were found to be the most active compounds, with MIC values of 0.08 µmol mL-1. The newly synthesized thiadiazole and triazole compounds (compounds 10-23) showed promising anti-Candida activity. The allyl substituent-bearing compounds 11 and 18 exhibited significant anti-Candida albicans activity and showed a binding mode as well as the fluconazole x-ray structure.Universidade de São Paulo. Faculdade de Ciências Farmacêuticas2017-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://www.revistas.usp.br/bjps/article/view/13142510.1590/s2175-97902017000115239Brazilian Journal of Pharmaceutical Sciences; Vol. 53 Núm. 1 (2017); e15239-Brazilian Journal of Pharmaceutical Sciences; v. 53 n. 1 (2017); e15239-Brazilian Journal of Pharmaceutical Sciences; Vol. 53 No. 1 (2017); e15239-2175-97901984-8250reponame:Brazilian Journal of Pharmaceutical Sciencesinstname:Universidade de São Paulo (USP)instacron:USPenghttps://www.revistas.usp.br/bjps/article/view/131425/127805Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso)info:eu-repo/semantics/openAccessRadwan, Awwad AbdohAlanazi, Fares KaedAl-Agamy, Mohammed Hamed2017-04-20T20:28:50Zoai:revistas.usp.br:article/131425Revistahttps://www.revistas.usp.br/bjps/indexPUBhttps://old.scielo.br/oai/scielo-oai.phpbjps@usp.br||elizabeth.igne@gmail.com2175-97901984-8250opendoar:2017-04-20T20:28:50Brazilian Journal of Pharmaceutical Sciences - Universidade de São Paulo (USP)false |
dc.title.none.fl_str_mv |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
title |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
spellingShingle |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans Radwan, Awwad Abdoh Anti-Candida/docking studies Thiadiazole Triazole |
title_short |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
title_full |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
title_fullStr |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
title_full_unstemmed |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
title_sort |
1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans |
author |
Radwan, Awwad Abdoh |
author_facet |
Radwan, Awwad Abdoh Alanazi, Fares Kaed Al-Agamy, Mohammed Hamed |
author_role |
author |
author2 |
Alanazi, Fares Kaed Al-Agamy, Mohammed Hamed |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Radwan, Awwad Abdoh Alanazi, Fares Kaed Al-Agamy, Mohammed Hamed |
dc.subject.por.fl_str_mv |
Anti-Candida/docking studies Thiadiazole Triazole |
topic |
Anti-Candida/docking studies Thiadiazole Triazole |
description |
Dramatically increased occurrence of both superficial and invasive fungal infections has been observed. Candida albicans appear to be the main etiological agent of invasive fungal infections. The anti-C. albicans activity of thiosemicarbazide, 1,3,4-Thiadiazole, and 1,2,4-triazole-3(4H)-thione compounds (compounds 3-23) were investigated. The MIC values of thiadiazole and triazole derivatives 10-23 were in the range of 0.08-0.17 µmol mL-1, while that of fluconazole was 0.052 µmol mL-1. Compound 11 (5-(2-(4-chlorobenzyloxy)phenyl)-N-allyl-1,3,4-thiadiazol-2-amine) and compound 18 (5-(2-(4-chlorobenzyloxy)phenyl)-4-allyl-2H-1,2,4-triazole-3(4H)-thione) were found to be the most active compounds, with MIC values of 0.08 µmol mL-1. The newly synthesized thiadiazole and triazole compounds (compounds 10-23) showed promising anti-Candida activity. The allyl substituent-bearing compounds 11 and 18 exhibited significant anti-Candida albicans activity and showed a binding mode as well as the fluconazole x-ray structure. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-01-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://www.revistas.usp.br/bjps/article/view/131425 10.1590/s2175-97902017000115239 |
url |
https://www.revistas.usp.br/bjps/article/view/131425 |
identifier_str_mv |
10.1590/s2175-97902017000115239 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
https://www.revistas.usp.br/bjps/article/view/131425/127805 |
dc.rights.driver.fl_str_mv |
Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso) info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Copyright (c) 2018 Brazilian Journal of Pharmaceutical Sciences (Impresso) |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade de São Paulo. Faculdade de Ciências Farmacêuticas |
publisher.none.fl_str_mv |
Universidade de São Paulo. Faculdade de Ciências Farmacêuticas |
dc.source.none.fl_str_mv |
Brazilian Journal of Pharmaceutical Sciences; Vol. 53 Núm. 1 (2017); e15239- Brazilian Journal of Pharmaceutical Sciences; v. 53 n. 1 (2017); e15239- Brazilian Journal of Pharmaceutical Sciences; Vol. 53 No. 1 (2017); e15239- 2175-9790 1984-8250 reponame:Brazilian Journal of Pharmaceutical Sciences instname:Universidade de São Paulo (USP) instacron:USP |
instname_str |
Universidade de São Paulo (USP) |
instacron_str |
USP |
institution |
USP |
reponame_str |
Brazilian Journal of Pharmaceutical Sciences |
collection |
Brazilian Journal of Pharmaceutical Sciences |
repository.name.fl_str_mv |
Brazilian Journal of Pharmaceutical Sciences - Universidade de São Paulo (USP) |
repository.mail.fl_str_mv |
bjps@usp.br||elizabeth.igne@gmail.com |
_version_ |
1800222912918061056 |