The influence of halogen substituents on the biological properties of sulfur-containing flavonoids.
A series of halogen-substituted tricyclic flavonoids containing a 1,3-dithiol-2-ylium moiety has been synthesized from the corresponding 3-dithiocarbamic flavanones. The influence of halogen substituents on the antibacterial properties of the tricyclic flavonoids has been investigated against Staphylococcus aureus and Escherichia coli. On going from fluorine to iodine, these compounds exhibit good to excellent inhibitory properties against both Gram-positive and Gram-negative pathogens. These results suggest that size is the main factor for the change in potency rather than polarity/electronics.
Department of Chemistry, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania; Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Lucian Gabriel
LG
Bahrin
Department of Chemistry, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania.
Laura Gabriela
LG
Sarbu
Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Henning
H
Hopf
Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
Peter G
PG
Jones
Department of Biology, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania.
Cornelia
C
Babii
Department of Biology, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania. Electronic address: stefanm@uaic.ro.
Marius
M
Stefan
Department of Chemistry, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania; Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany. Electronic address: lbirsa@uaic.ro.
Mihail Lucian
ML
Birsa
D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004926:Escherichia coli / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D006219:Halogens / Q000737:chemistry*; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D066244:Proton Magnetic Resonance Spectroscopy; D013211:Staphylococcus aureus / Q000187:drug effects; D013455:Sulfur / Q000737:chemistry*
D005419:Flavonoids; D006219:Halogens; D013455:Sulfur
Aminals; Antibacterial activity; Dithiocarbamates; Dithiolium salts; Flavonoids