Investigation of 5-Nitrofuran Derivatives: Synthesis, Antibacterial Activity, and Quantitative Structure−Activity Relationships

• DOI: 10.1021/jm0101693
• Publication Date: 2002-07-26T04:41:49Z
• Authors: José Ricardo Pires; Cristina Saito; Suely L. Gomes; Astréa M. Giesbrecht; Antonia T-do Amaral
• Keywords: Caulobacter crescentus; Nitrofuran; Strain (injury)

Three sets of antibacterial nitrofuran derivatives [set I, 5-R-substituted (Z)-2-(5-nitrofuran-2-ylmethylene)-3(2H)-benzofuranones (R = OCH3, H, CH3, C2H5, nC3H7, Cl, Br, CN, and NO2) their 2-hydroxyphenyl 2-acetoxyphenyl analogues; set II, (E)-1-(2-hydroxyphenyl)-3-(5-nitrofuryl)-2-propen-1-ones NO2); III, (E)-1-(2-acetoxyphenyl)-3-(5-nitrofuryl)-2-propen-1-ones CH3; NO2)] were prepared tested against a Gram-positive (Staphylococcus aureus, strain ATCC-25923) Gram-negative bacterium (Caulobacter crescentus, NA 1000). QSAR equations derived for the IC50 values both bacteria show negative contributions two terms: an electronic one, expressed either by σ, Hammett substituent constant, or E, cyclic voltametric reduction potential. Another term described indicator variable, Iabs, is assigned value 0 I compounds 1 II III. No important contribution hydrophobic factor was found. For three sets, regressions suggest that same structural features describe activities that, although necessary step, it should not be determining one. These results agree with those found 5-nitroimidazole analogues.