PMID: 11606132Oct 19, 2001Paper

Investigation of 5-nitrofuran derivatives: synthesis, antibacterial activity, and quantitative structure-activity relationships

Journal of Medicinal Chemistry
J R PiresA T Amaral

Abstract

Three sets of antibacterial nitrofuran derivatives [set I, 5-R-substituted (Z)-2-(5-nitrofuran-2-ylmethylene)-3(2H)-benzofuranones (R = OCH(3), H, CH(3), C(2)H(5), nC(3)H(7), Cl, Br, CN, and NO(2)) and their 2-hydroxyphenyl and 2-acetoxyphenyl analogues; set II, 5-R-substituted (E)-1-(2-hydroxyphenyl)-3-(5-nitrofuryl)-2-propen-1-ones (R = H, CH(3), C(2)H(5), Cl, and NO(2)); and set III, 5-R-substituted (E)-1-(2-acetoxyphenyl)-3-(5-nitrofuryl)-2-propen-1-ones (R = H, CH(3); C(2)H(5), Cl, and NO(2))] were prepared and tested against a Gram-positive (Staphylococcus aureus, strain ATCC-25923) and a Gram-negative bacterium (Caulobacter crescentus, strain NA 1000). QSAR equations derived for the IC(50) values against both bacteria show negative contributions of two terms: an electronic one, expressed either by sigma, the Hammett substituent constant, or by E, the cyclic voltametric reduction potential. Another term described by an indicator variable, I(abs), is assigned the value of 0 for set I compounds and the value of 1 for sets II and III. No important contribution of the hydrophobic factor was found. For the three sets, the QSAR regressions suggest that the same structural features describe the activities for both bacteria and t...Continue Reading

References

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Citations

Jul 15, 2015·Biological & Pharmaceutical Bulletin·Hatem Abdel-Kader Abdel-AzizDalia Hussein Soliman
Dec 20, 2005·Bioorganic & Medicinal Chemistry Letters·Alireza ForoumadiAbbas Shafiee
Feb 25, 2006·Bioorganic & Medicinal Chemistry·Nuno MilhazesFernanda Borges
Jun 22, 2007·Chemical Biology & Drug Design·Bahram HemmateenejadAbbas Shafiee
Jan 14, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Keshri Nath TiwariClaude Jolivalt
Jun 29, 2010·Journal of Enzyme Inhibition and Medicinal Chemistry·Eskandar AlipourAlireza Foroumadi
Oct 28, 2008·Journal of Enzyme Inhibition and Medicinal Chemistry·Ahmed KamalU S N Murthy
Jun 9, 2020·Frontiers in Microbiology·Dong YangYing Kong
Nov 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Renzo Rossi, Maurizio Ciofalo
Apr 21, 2019·Experimental Parasitology·Aline Cavalcanti de QueirozMagna Suzana Alexandre-Moreira
Jan 22, 2019·European Journal of Medicinal Chemistry·Hamza OlleikRomain Haudecoeur
Oct 1, 2021·Chemical Society Reviews·Jana VolarićBen L Feringa

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