New Substituted Benzoylthiourea Derivatives: From Design to Antimicrobial Applications
Carmen Limban,
Mariana Carmen Chifiriuc,
Miron Teodor Caproiu,
Florea Dumitrascu,
Marilena Ferbinteanu,
Lucia Pintilie,
Amalia Stefaniu,
Ilinca Margareta Vlad,
Coralia Bleotu,
Luminita Gabriela Marutescu,
Diana Camelia Nuta
Affiliations
Carmen Limban
Department of Pharmaceutical Chemistry, “Carol Davila” University of Medicine and Pharmacy, 020956 Bucharest, Romania
Mariana Carmen Chifiriuc
Department of Microbiology, Faculty of Biology & Research Institute of the University of Bucharest (ICUB), University of Bucharest, 060101 Bucharest, Romania
Miron Teodor Caproiu
The Organic Chemistry Center of Romanian Academy “C. D. Neniţescu”, 060023 Bucharest, Romania
Florea Dumitrascu
The Organic Chemistry Center of Romanian Academy “C. D. Neniţescu”, 060023 Bucharest, Romania
Marilena Ferbinteanu
Inorganic Chemistry Department, Faculty of Chemistry, University of Bucharest, 020462 Bucharest, Romania
Lucia Pintilie
National Institute of Chemical-Pharmaceutical Research & Development, 031299 Bucharest, Romania
Amalia Stefaniu
National Institute of Chemical-Pharmaceutical Research & Development, 031299 Bucharest, Romania
Ilinca Margareta Vlad
Department of Pharmaceutical Chemistry, “Carol Davila” University of Medicine and Pharmacy, 020956 Bucharest, Romania
Coralia Bleotu
Stefan S. Nicolau Institute of Virology, Mihai Bravu 285, Bucharest, 030304, Romania
Luminita Gabriela Marutescu
Department of Microbiology, Faculty of Biology & Research Institute of the University of Bucharest (ICUB), University of Bucharest, 060101 Bucharest, Romania
Diana Camelia Nuta
Department of Pharmaceutical Chemistry, “Carol Davila” University of Medicine and Pharmacy, 020956 Bucharest, Romania
The increasing threat of antimicrobial resistance to all currently available therapeutic agents has urged the development of novel antimicrobials. In this context, a series of new benzoylthiourea derivatives substituted with one or more fluorine atoms and with the trifluoromethyl group have been tested, synthesized, and characterized by IR, NMR, CHNS and crystal X-ray diffraction. The molecular docking has provided information regarding the binding affinity and the orientation of the new compounds to Escherichia coli DNA gyrase B. The docking score predicted the antimicrobial activity of the studied compounds, especially against E. coli, which was further demonstrated experimentally against planktonic and biofilm embedded bacterial and fungal cells. The compounds bearing one fluorine atom on the phenyl ring have shown the best antibacterial effect, while those with three fluorine atoms exhibited the most intensive antifungal activity. All tested compounds exhibited antibiofilm activity, correlated with the trifluoromethyl substituent, most favorable in para position.
