Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides.
A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 μΜ), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 μM). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 μM) and low toxicity to normal cells (CC50=157.83 μM). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates.
Instituto de Química, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Thiago Belarmino
TB
de Souza
Centro Universitário de Lavras, 37200-000, MG, Brazil.
Paulo Otávio Botelho
PO
Raimundo
Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, 90610-000, RS, Brazil.
Saulo Fernandes
SF
Andrade
Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Taciane Maira Magalhães
TM
Hipólito
Instituto de Ciências Biomédicas, Departamento de Microbiologia e Imunologia, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Naiara Chaves
NC
Silva
Instituto de Ciências Biomédicas, Departamento de Microbiologia e Imunologia, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Amanda Latercia Tranches
AL
Dias
Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Masaharu
M
Ikegaki
Instituto de Ciências Biomédicas, Departamento de Microbiologia e Imunologia, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Raissa Prado
RP
Rocha
Instituto de Ciências Biomédicas, Departamento de Microbiologia e Imunologia, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Luiz Felipe Leomil
LF
Coelho
Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Marcia Paranho
MP
Veloso
Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, 37130-000, MG, Brazil.
Diogo Teixeira
DT
Carvalho
Instituto de Química, Universidade Federal de Alfenas, 37130-000, MG, Brazil. Electronic address: danielle.dias@unifal-mg.edu.br.
Danielle Ferreira
DF
Dias
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D005054:Eugenol / Q000138:chemical synthesis* / Q000494:pharmacology*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D016982:Micrococcus luteus / Q000187:drug effects; D012486:Salmonella typhimurium / Q000187:drug effects; D014230:Triazoles / Q000737:chemistry
D000890:Anti-Infective Agents; D005960:Glucosides; D014230:Triazoles; D005054:Eugenol
Antimicrobial activity; Eugenol glucosides; Triazoles