The influence of halogen substituents on the biological properties of sulfur-containing flavonoids

Lucian Gabriel Bahrin; Laura Gabriela Sarbu; Henning Hopf; Peter G Jones; Cornelia Babii; Marius Stefan; Mihail Lucian Birsa

doi:10.1016/j.bmc.2016.05.044

The influence of halogen substituents on the biological properties of sulfur-containing flavonoids

Bioorg Med Chem. 2016 Jul 15;24(14):3166-73. doi: 10.1016/j.bmc.2016.05.044. Epub 2016 May 24.

Authors

Lucian Gabriel Bahrin¹, Laura Gabriela Sarbu², Henning Hopf³, Peter G Jones⁴, Cornelia Babii⁵, Marius Stefan⁶, Mihail Lucian Birsa⁷

Affiliations

¹ 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.
² Department of Chemistry, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania.
³ Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
⁴ Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
⁵ Department of Biology, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania.
⁶ Department of Biology, Al.I. Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania. Electronic address: stefanm@uaic.ro.
⁷ 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.

PMID: 27259400
DOI: 10.1016/j.bmc.2016.05.044

Abstract

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.

Keywords: Aminals; Antibacterial activity; Dithiocarbamates; Dithiolium salts; Flavonoids.

MeSH terms

Carbon-13 Magnetic Resonance Spectroscopy
Escherichia coli / drug effects
Flavonoids / chemistry*
Flavonoids / pharmacology
Halogens / chemistry*
Mass Spectrometry
Microbial Sensitivity Tests
Proton Magnetic Resonance Spectroscopy
Staphylococcus aureus / drug effects
Sulfur / chemistry*

Substances

Flavonoids
Halogens
Sulfur