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Synthesis and Antibacterial Activity of Substituted Oxotriazolylphenyl Oxazolidinones
Author(s) -
Liu Jidong,
He Baoyuan,
Yu Aizhen,
Zhou Weicheng
Publication year - 2007
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2007.00531.x
Subject(s) - antibacterial activity , staphylococcus epidermidis , streptococcus pneumoniae , streptococcus , chemistry , agar dilution , minimum inhibitory concentration , gram , gram positive bacteria , agar , stereochemistry , staphylococcus aureus , in vitro , microbiology and biotechnology , bacteria , organic chemistry , biology , antimicrobial , biochemistry , antibiotics , genetics
A series of 3‐(4′‐(2′′‐alkyl‐3′′‐oxy‐1′′,2′′,4′′‐triazolyl)‐phenyl)‐5‐substituted oxazolidinones was designed and synthesized for in vitro antibacterial activity testing against fourteen Gram‐negative and six Gram‐positive standard organisms. The minimum inhibitory concentration (MIC) was determined by agar dilution at concentrations of 0.10, 0.20, 0.39, 0.78, 1.56, 3.13, 6.25 μ g/mL. Different alkyl groups at the 2′′‐position played an important role in the activity against Gram‐positive organisms. (S)‐3‐(4′‐(2′′‐ethyl‐3′′‐oxy‐1′′,2′′,4′′‐triazolyl)‐phenyl)‐5‐acetamidomethyloxazolidinone was active against Staphylococcus epidermidis, Streptococcus pneumoniae, Streptococcus enteridis and Streptococcus nonhemolyticus , whereas 2′′‐methyl, 2′′‐propyl and 2′′‐ n ‐butyl counterparts did not show activity at 6.25 μ g/mL. Modification of the 5‐substitutent of oxazolidinones also affected the activity against Gram‐positive organisms. (S)‐3‐(4′‐(2′′‐ethyl‐3′′‐oxy‐1′′,2′′,4′′‐triazolyl)‐phenyl)‐5‐acetamidomethyloxazolidinones was approximately two fold more potent than 5‐chloroacetamido, 5‐dichloroacetamido and 5‐trifluoroacetamido counterparts against Streptococcus enteridis . None of these compounds showed growth inhibition against fourteen Gram‐negative organisms at 6.25 μ g/mL.