Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/26031
Title: Synthesis of piplartine analogs and preliminary findings on structure–antimicrobial activity relationship
Authors: Fregnan, Antonio Maciel
Brancaglion, Guilherme Andrade
Galvão, Alexandre Francisco Cerqueira
Costa, Cinara Oliveira D’Sousa
Moreira, Diogo Rodrigo Magalhães
Soares, Milena Botelho Pereira
Bezerra, Daniel Pereira
Silva, Naiara Chaves
Morais, Stella Maria de Souza
Oliver, Josidel Conceição
Dias, Amanda Latercia Tranches
Coelho, Luiz Felipe Leomil
Carvalho, Diogo Teixeira
Dias, Danielle Ferreira
Souza, Thiago Belarmino de
Affilliation: Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil
Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil
Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Ciências Biomédicas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Faculdade de Ciências Farmacêuticas. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil
Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil
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.
Keywords: Piplartine
Analogs
Antifungal activity
Antibacterial activity
keywords: Piplartina
Análogos
Atividade antifúngica
Atividade antibacteriana
Issue Date: 2017
Publisher: Springer Verlag
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.
ISSN: 1054-2523
Copyright: open access
Appears in Collections:BA - IGM - Artigos de Periódicos

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