Author | Fregnan, Antonio Maciel | |
Author | Brancaglion, Guilherme Andrade | |
Author | Galvão, Alexandre Francisco Cerqueira | |
Author | Costa, Cinara Oliveira D’Sousa | |
Author | Moreira, Diogo Rodrigo Magalhães | |
Author | Soares, Milena Botelho Pereira | |
Author | Bezerra, Daniel Pereira | |
Author | Silva, Naiara Chaves | |
Author | Morais, Stella Maria de Souza | |
Author | Oliver, Josidel Conceição | |
Author | Dias, Amanda Latercia Tranches | |
Author | Coelho, Luiz Felipe Leomil | |
Author | Carvalho, Diogo Teixeira | |
Author | Dias, Danielle Ferreira | |
Author | Souza, Thiago Belarmino de | |
Access date | 2018-04-23T14:32:48Z | |
Available date | 2018-04-23T14:32:48Z | |
Document date | 2017 | |
Citation | FREGNAN, A. M. et al. Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship. Medicinal Chemistry Research, v. 26, p. 603–614, 2017. | pt_BR |
ISSN | 1054-2523 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/26031 | |
Sponsorship | FAPEMIG (APQ-01209-13), CAPES, CNPq and FINEP. | pt_BR |
Language | eng | pt_BR |
Publisher | Springer Verlag | pt_BR |
Rights | open access | pt_BR |
Subject in Portuguese | Piplartina | pt_BR |
Subject in Portuguese | Análogos | pt_BR |
Subject in Portuguese | Atividade antifúngica | pt_BR |
Subject in Portuguese | Atividade antibacteriana | pt_BR |
Title | Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship | pt_BR |
Type | Article | pt_BR |
Abstract | Abstract In this work it is described the synthesis, characterization
and antimicrobial and toxicity evaluation of a
series of analogs of piplartine, a piperamide found in Piper
sp. The compounds structures were confirmed by infrared
spectroscopy, 1H, 13C nuclear magnetic resonance, high
resolution mass spectroscopy and were evaluated against
strains of Candida spp., Staphylococcus aureus, Escherichia
coli and Pseudomonas aeruginosa. Derivative 24 was
almost four-fold more potent (IC50: 48.83 μM) and five-fold
less toxic (SI > 3) than piplartine (IC50: 189.2 μM; SI: 0.21)
against Candida krusei, as well as two-fold more potent
than fluconazole (IC50: 104.48 μM). This compound was
also active against Candida tropicalis at 97.67 μM. Benzoyl
derivative 17 was three-fold more potent (IC50: 85.2 μM)
and more than five-fold less toxic (CC50: 231.71 μM) than
piplartine (IC50: 315.33 μM and CC50: 41.14 μM) against
Staphylococcus aureus. Given these findings, we have
found analogs of piplartine which can be assumed as prototypes
for the optimization and the development of new
antimicrobial (compounds 24 and 17) agents. | pt_BR |
Affilliation | Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil | pt_BR |
Affilliation | Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil | pt_BR |
Subject | Piplartine | pt_BR |
Subject | Analogs | pt_BR |
Subject | Antifungal activity | pt_BR |
Subject | Antibacterial activity | pt_BR |